v0.2.53 - Add signer_health.c to Dockerfile.alpine-musl source list (was missing, causing static build failure)

Dockerfile.alpine-musl

@@ -123,7 +123,7 @@ RUN NOSTR_LIB=$(ls /build/nostr_core_lib/libnostr_core_*.a 2>/dev/null | head -1
     src/tools/tool_task.c src/tools/tool_nostr_list.c src/tools/tool_nostr_block.c src/tools/tool_local.c \
     src/tools/tool_skill.c src/tools/tool_nostr_post.c src/tools/tool_memory.c src/tools/tool_config.c src/tools/tool_cashu_wallet.c src/tools/tool_blossom.c src/trigger_manager.c \
     src/cashu_wallet.c src/nostr_block_list.c src/prompt_template.c src/http_api.c src/setup_wizard.c src/mongoose.c src/debug.c \
-    src/json_to_markdown.c src/context_roles.c src/context_format.c \
+    src/json_to_markdown.c src/context_roles.c src/context_format.c src/signer_health.c \
     -o /build/didactyl_static \
     $NOSTR_LIB \
     -lsecp256k1 \

Makefile

@@ -1,5 +1,5 @@
 CC = gcc
-CFLAGS = -std=c99 -Wall -Wextra -Wpedantic -O2 -D_GNU_SOURCE -D_DEFAULT_SOURCE -D_POSIX_C_SOURCE=200809L -DMG_TLS=MG_TLS_BUILTIN
+CFLAGS = -std=c99 -Wall -Wextra -Wpedantic -O2 -D_GNU_SOURCE -D_DEFAULT_SOURCE -D_POSIX_C_SOURCE=200809L -DMG_TLS=MG_TLS_BUILTIN -DNOSTR_ENABLE_NSIGNER_CLIENT=1
 
 SRC_DIR = src
 TARGET = didactyl
@@ -44,7 +44,8 @@ SRCS = \
 	$(SRC_DIR)/nostr_block_list.c \
 	$(SRC_DIR)/json_to_markdown.c \
 	$(SRC_DIR)/context_roles.c \
-	$(SRC_DIR)/context_format.c
+	$(SRC_DIR)/context_format.c \
+	$(SRC_DIR)/signer_health.c
 
 INCLUDES = \
 	-I$(SRC_DIR) \

README.md

@@ -54,11 +54,11 @@ Skills compose by adoption-list order (`10123`) and trigger tags carry runtime e
 
 Didactyl will support local inference, which is very privacy preserving. Remote inference does however have it's advantages, and in those cases Didactyl supports using Bitcoin Lightning and eCash inference providers.
 
-## Current Status — v0.2.35
+## Current Status — v0.2.53
 
 **Active build — this project is barely working. Experiment at your own risk.**
 
-> Last release update: v0.2.35 — Remove top-level dm_protocol from genesis configs and set user-settings kind 30078 dm_protocol to both
+> Last release update: v0.2.53 — Add signer_health.c to Dockerfile.alpine-musl source list (was missing, causing static build failure)
 
 - Connects to configured relays with auto-reconnect and relay state transition logging
 - Publishes configured startup events per relay as each relay becomes connected

context.logs/20260428T071923_res0001.json

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context.logs/20260428T071928_res0002.json

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context.logs/20260428T072036_res0003.json

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+{"id":"gen-1777375237-UNuX3x5bOLRo3Yf2fhGV","object":"chat.completion","created":1777375237,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"I'm ready to help! I'm a test agent running on the Didactyl platform. I have access to a comprehensive set of tools for:\n\n- **Nostr operations**: posting, querying, reactions, DMs, profiles, relays, encryption\n- **File management**: reading and writing local files\n- **Skills**: creating, managing, and executing skills\n- **LLM configuration**: managing model settings and parameters\n- **Wallet**: Cashu ecash wallet operations\n- **Storage**: Blossom file uploads/downloads\n- **Utilities**: shell execution, HTTP requests, version info\n\nFeel free to ask me to:\n- Post to Nostr\n- Query events or profiles\n- Manage skills and tasks\n- Read/write files\n- Execute shell commands\n- Work with encrypted storage\n- Or anything else you'd like to test!\n\nWhat would you like me to do?","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":9354,"completion_tokens":199,"total_tokens":9553,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":0,"cache_write_tokens":9351,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.01268675,"upstream_inference_prompt_cost":0.01169175,"upstream_inference_completions_cost":0.000995},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T072050_res0001.json

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context.logs/20260428T072113_res0001.json

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context.logs/20260428T072117_res0002.json

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context.logs/20260428T072221_res0003.json

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context.logs/20260428T072235_res0001.json

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+{"id":"gen-1777375355-ZuuW9IXNHn2xcCnAxE0y","object":"chat.completion","created":1777375355,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"tool_calls","native_finish_reason":"tool_use","message":{"role":"assistant","content":"I'll check your Cashu wallet balance for you.","refusal":null,"reasoning":null,"tool_calls":[{"type":"function","index":0,"id":"toolu_bdrk_01AjyEY1765A49f2DE6Uh3GG","function":{"name":"cashu_wallet_balance","arguments":"{}"}}]}}],"usage":{"prompt_tokens":9368,"completion_tokens":52,"total_tokens":9420,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":9032,"cache_write_tokens":332,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.0015822,"upstream_inference_prompt_cost":0.0013222,"upstream_inference_completions_cost":0.00026},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T072238_res0002.json

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context.logs/20260428T072342_res0003.json

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context.logs/20260428T072356_res0001.json

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context.logs/20260428T072358_res0002.json

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context.logs/20260428T072501_res0003.json

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context.logs/20260428T072515_res0001.json

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context.logs/20260428T072518_res0002.json

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context.logs/20260428T072621_res0003.json

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context.logs/20260428T072636_res0001.json

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context.logs/20260428T072640_res0002.json

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context.logs/20260428T072743_res0003.json

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context.logs/20260428T072756_res0001.json

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context.logs/20260428T072759_res0002.json

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context.logs/20260428T072815_res0003.json

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context.logs/20260428T072855_res0001.json

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context.logs/20260428T072900_res0002.json

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context.logs/20260428T072935_res0003.json

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context.logs/20260428T072949_res0001.json

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context.logs/20260428T073009_res0001.json

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context.logs/20260428T073013_res0002.json

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+{"id":"gen-1777375813-DRu7RouOiJlA3MKNwdc3","object":"chat.completion","created":1777375813,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"I'm **Didactyl**, a Nostr-based AI agent. Here's a brief description of what I am:\n\n## Core Identity\n- A decentralized autonomous agent that operates on the Nostr protocol\n- I can publish, query, and interact with Nostr events across multiple relays\n- I have my own pubkey and can act independently or on behalf of an admin user\n\n## Key Capabilities\n- **Nostr Integration**: Publish notes, long-form posts, reactions, and encrypted DMs\n- **Skill System**: I can create, adopt, and execute specialized skills (reusable AI workflows)\n- **Task Management**: Track and manage tasks stored on Nostr\n- **Memory**: I maintain encrypted agent memory for continuity across conversations\n- **LLM Integration**: I'm powered by configurable language models (currently using an OpenAI-compatible backend)\n- **Wallet & Payments**: I can manage Cashu ecash wallets and handle Lightning payments\n- **File Operations**: I can read/write files and interact with Blossom file storage servers\n- **Web Integration**: I can fetch HTTP resources and execute shell commands\n\n## How I Work\nI respond to requests and use tools when needed. I can be triggered by:\n- Direct messages (DMs)\n- Scheduled tasks (cron jobs)\n- Nostr subscriptions\n- Webhooks\n- Skill chains\n\nI'm designed to be privacy-respecting, leveraging Nostr's encryption where appropriate, and can operate autonomously or collaboratively with an admin user.\n\nWhat would you like to know more about, or how can I help you?","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":9373,"completion_tokens":365,"total_tokens":9738,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":9370,"cache_write_tokens":0,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.002765,"upstream_inference_prompt_cost":0.00094,"upstream_inference_completions_cost":0.001825},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T073119_res0003.json

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+{"id":"gen-1777375880-ECGT0ZdA9f6YOQOw8lM9","object":"chat.completion","created":1777375880,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"I'm ready to help! I'm a Didactyl agent designed to assist you with various tasks using the available tools.\n\nI can help you with:\n\n- **Nostr Operations**: Post notes, query events, manage profiles, send DMs, handle encryption, manage lists and block lists\n- **Skill Management**: Create, edit, list, search, and run skills\n- **Local Operations**: Read/write files, execute shell commands, fetch HTTP resources\n- **Agent Configuration**: Manage LLM settings, model selection, and runtime configuration\n- **Memory & Tasks**: Store and recall agent memory, manage task lists\n- **Wallet Operations**: Check balances, mint/melt ecash, send/receive tokens\n- **File Storage**: Upload/download files via Blossom servers\n- **Relay Management**: Check relay status, fetch relay info, manage subscriptions\n\nWhat would you like me to help you with?","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":9354,"completion_tokens":203,"total_tokens":9557,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":9351,"cache_write_tokens":0,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.0019531,"upstream_inference_prompt_cost":0.0009381,"upstream_inference_completions_cost":0.001015},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T073133_res0001.json

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+{"id":"gen-1777375894-scuuv4LZNWVF29yV05L7","object":"chat.completion","created":1777375894,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"I see you've sent a very long string of the letter \"A\". \n\nI'm a test agent here to help you with requests and use tools when needed. Is there something specific I can help you with? Feel free to ask me a question or let me know what you'd like to do, and I'll do my best to assist using the available tools.","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":16024,"completion_tokens":78,"total_tokens":16102,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":16024,"cache_write_tokens":0,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.0019924,"upstream_inference_prompt_cost":0.0016024,"upstream_inference_completions_cost":0.00039},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T073347_res0001.json

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+{"id":"gen-1777376029-xUzuqdFfKe7nM3xi1ooh","object":"chat.completion","created":1777376029,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"Hello! 👋 I'm the Didactyl test agent, and I'm ready to help. I received your message: \"Hello from smoke test\"\n\nI have access to a wide range of tools including:\n\n- **Nostr Protocol Tools** - posting, querying, DMs, profiles, relays, etc.\n- **File Operations** - reading and writing local files\n- **Shell Commands** - executing commands\n- **Skills Management** - creating, editing, and running skills\n- **HTTP Requests** - fetching web resources\n- **Cashu Wallet** - ecash operations\n- **Blossom** - file storage/retrieval\n- **Configuration & Memory** - storing and recalling agent state\n\nWhat would you like me to help you with? Feel free to ask me to:\n- Post to Nostr\n- Query events or profiles\n- Manage files\n- Run commands\n- Create or manage skills\n- Handle any other tasks you need","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":9364,"completion_tokens":216,"total_tokens":9580,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":9032,"cache_write_tokens":328,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.0023972,"upstream_inference_prompt_cost":0.0013172,"upstream_inference_completions_cost":0.00108},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

context.logs/20260428T073359_res0001.json

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+
+         
+{"id":"gen-1777376040-qkXhEUESTodU6M3rpqhw","object":"chat.completion","created":1777376040,"model":"anthropic/claude-4.5-haiku-20251001","provider":"Amazon Bedrock","system_fingerprint":null,"choices":[{"index":0,"logprobs":null,"finish_reason":"stop","native_finish_reason":"end_turn","message":{"role":"assistant","content":"Hello! I'm ready to help you with any requests you might have.","refusal":null,"reasoning":null}}],"usage":{"prompt_tokens":9367,"completion_tokens":18,"total_tokens":9385,"cost":0,"is_byok":true,"prompt_tokens_details":{"cached_tokens":9032,"cache_write_tokens":332,"audio_tokens":0,"video_tokens":0},"cost_details":{"upstream_inference_cost":0.0014112,"upstream_inference_prompt_cost":0.0013212,"upstream_inference_completions_cost":0.00009},"completion_tokens_details":{"reasoning_tokens":0,"image_tokens":0,"audio_tokens":0}}}

didactyl.pid

@@ -0,0 +1 @@
+131350

didactyl_nsigner.log

@@ -0,0 +1,70 @@
+Didactyl - sovereign Nostr agent
+
+Usage:
+  ./didactyl [options]
+
+Options:
+  -h, --help
+      Show this help text and exit.
+  -v, --version
+      Show version and exit.
+  --config <path>
+      Path to config/genesis JSONC file (default: ./genesis.jsonc).
+      If file is missing, startup falls back to minimal nsec-only mode.
+  --nsec <nsec_or_hex>
+      Private key as nsec1... or 64-char hex; overrides DIDACTYL_NSEC.
+  --admin <npub_or_hex>
+      Administrator pubkey override; accepts npub1... or 64-char hex.
+  --api-port <port>
+      Enable HTTP API and bind to this port (1-65535).
+  --api-bind <addr>
+      Enable HTTP API and bind address (example: 127.0.0.1).
+  --debug <0-5>
+      Log level (0=fatal, 1=error, 2=warn, 3=info, 4=debug, 5=trace).
+  --signer <mode>
+      Signer provider: local | nsigner_unix | nsigner_tcp.
+      Overrides signer.mode in config and DIDACTYL_SIGNER.
+      In nsigner_* modes --nsec/DIDACTYL_NSEC are not required.
+  --signer-socket <name>
+      Abstract socket name for nsigner_unix (without leading @).
+  --signer-role <role>
+      n_signer role selector (default: main).
+  --signer-timeout <ms>
+      Per-call signer timeout in milliseconds (default: 15000).
+  --signer-tcp <host:port>
+      Shorthand for --signer nsigner_tcp with host/port parsed.
+  --dump-schemas
+      Print tool schemas JSON and exit.
+  --test-tool <name> <args_json>
+      Execute one tool call locally and print JSON result, then exit.
+
+Environment:
+  DIDACTYL_NSEC
+      Fallback private key when --nsec is not provided (local mode only).
+  DIDACTYL_SIGNER
+      Fallback signer mode when --signer is not provided.
+
+Examples:
+  1) Genesis-based startup
+     ./didactyl --config genesis.jsonc
+
+  2) nsec-only startup (no config file)
+     ./didactyl --nsec nsec1...
+
+  3) nsec via environment variable
+     DIDACTYL_NSEC=nsec1... ./didactyl
+
+  4) Override API bind/port
+     ./didactyl --config genesis.jsonc --api-bind 127.0.0.1 --api-port 8484
+
+  5) Sign with a running n_signer (separate the nsec from the agent)
+     ./didactyl --signer nsigner_unix --signer-socket nsigner_hairy_dog --admin npub1...
+
+  6) n_signer via TCP
+     ./didactyl --signer-tcp 127.0.0.1:7777 --admin npub1...
+
+  7) Dump tool schemas
+     ./didactyl --dump-schemas
+
+  8) Test a tool invocation
+     ./didactyl --test-tool config_recall '{"config_name":"llm_config"}'

exit_code.txt

@@ -0,0 +1 @@
+1

help_output.txt

@@ -0,0 +1,70 @@
+Didactyl - sovereign Nostr agent
+
+Usage:
+  ./didactyl [options]
+
+Options:
+  -h, --help
+      Show this help text and exit.
+  -v, --version
+      Show version and exit.
+  --config <path>
+      Path to config/genesis JSONC file (default: ./genesis.jsonc).
+      If file is missing, startup falls back to minimal nsec-only mode.
+  --nsec <nsec_or_hex>
+      Private key as nsec1... or 64-char hex; overrides DIDACTYL_NSEC.
+  --admin <npub_or_hex>
+      Administrator pubkey override; accepts npub1... or 64-char hex.
+  --api-port <port>
+      Enable HTTP API and bind to this port (1-65535).
+  --api-bind <addr>
+      Enable HTTP API and bind address (example: 127.0.0.1).
+  --debug <0-5>
+      Log level (0=fatal, 1=error, 2=warn, 3=info, 4=debug, 5=trace).
+  --signer <mode>
+      Signer provider: local | nsigner_unix | nsigner_tcp.
+      Overrides signer.mode in config and DIDACTYL_SIGNER.
+      In nsigner_* modes --nsec/DIDACTYL_NSEC are not required.
+  --signer-socket <name>
+      Abstract socket name for nsigner_unix (without leading @).
+  --signer-role <role>
+      n_signer role selector (default: main).
+  --signer-timeout <ms>
+      Per-call signer timeout in milliseconds (default: 15000).
+  --signer-tcp <host:port>
+      Shorthand for --signer nsigner_tcp with host/port parsed.
+  --dump-schemas
+      Print tool schemas JSON and exit.
+  --test-tool <name> <args_json>
+      Execute one tool call locally and print JSON result, then exit.
+
+Environment:
+  DIDACTYL_NSEC
+      Fallback private key when --nsec is not provided (local mode only).
+  DIDACTYL_SIGNER
+      Fallback signer mode when --signer is not provided.
+
+Examples:
+  1) Genesis-based startup
+     ./didactyl --config genesis.jsonc
+
+  2) nsec-only startup (no config file)
+     ./didactyl --nsec nsec1...
+
+  3) nsec via environment variable
+     DIDACTYL_NSEC=nsec1... ./didactyl
+
+  4) Override API bind/port
+     ./didactyl --config genesis.jsonc --api-bind 127.0.0.1 --api-port 8484
+
+  5) Sign with a running n_signer (separate the nsec from the agent)
+     ./didactyl --signer nsigner_unix --signer-socket nsigner_hairy_dog --admin npub1...
+
+  6) n_signer via TCP
+     ./didactyl --signer-tcp 127.0.0.1:7777 --admin npub1...
+
+  7) Dump tool schemas
+     ./didactyl --dump-schemas
+
+  8) Test a tool invocation
+     ./didactyl --test-tool config_recall '{"config_name":"llm_config"}'

nsigner.log

@@ -0,0 +1,668 @@
+nsigner v0.0.33
+Seed phrase is valid and accepted.
+System is ready and waiting for connections on @didactyl_test_signer.
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+(none)
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+(none)
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120623 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120623 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120741 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120623 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON
+Roles
+Role                 Purpose      Curve        Selector     
+-------------------- ------------ ------------ ------------ 
+main                 nostr        secp256k1    nostr_index  
+
+Activity (latest first)
+0708-120741 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120623 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120609 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120554 uid:1000 get_public_key(main) ALLOWED:prompt
+0708-120532 uid:1000 get_public_key(main) ALLOWED:prompt
+                                
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+================================================================================
+                                n_signer v0.0.33                                
+================================================================================
+> Main Menu
+
+
+Connections
+listen: unix @didactyl_test_signer
+client: nsigner --socket-name didactyl_test_signer client '<json>'
+fips ipv6: fdb8:36ad:c97a:44a9:e70e:e591:5d53:8f28
+fips npub: npub10vt4scusw6lq27qw83nfwp5sqer492h0tnwa8ugqjvp6l4xuz2qsdycrwd
+
+                                q/x quit
+                                l lock/reunlock
+                                r refresh
+                                A toggle auto-approve
+
+session=unlocked (12 words) signer=didactyl_test_signer derived=1 auto-approve=ON

nsigner.pid

@@ -0,0 +1 @@
+131270

plans/cron_trigger_robustness.md

@@ -0,0 +1,247 @@
+# Cron Trigger Pipeline: How It Works and How to Make It Robust
+
+## Current Architecture: Skill Events → Trigger Registration
+
+The pipeline has **two paths** for getting a cron trigger loaded, plus a **polling loop** that actually fires them.
+
+### Path 1: Bulk load at startup (EOSE-driven)
+
+```mermaid
+sequenceDiagram
+    participant Main as main.c startup
+    participant NH as nostr_handler
+    participant Relays as Nostr Relays
+    participant TM as trigger_manager
+
+    Main->>TM: trigger_manager_init - capacity=16, last_poll_at=0
+    Main->>TM: trigger_manager_load_from_startup_events
+    Note over TM: Loads triggers from genesis startup_events<br/>only dm triggers typically here
+    Main->>NH: nostr_handler_set_self_skill_eose_callback<br/>registers on_self_skill_eose_load_triggers
+    Main->>NH: nostr_handler_subscribe_self_skills
+    NH->>Relays: REQ kinds 31123, 31124, 10123<br/>authors = agent pubkey
+    Relays-->>NH: EVENT skill events arrive one by one
+    NH->>NH: on_self_skill_event for each<br/>caches in g_self_skill_events<br/>calls register_trigger_from_self_skill_event
+    Relays-->>NH: EOSE
+    NH->>NH: on_self_skill_eose sets g_self_skill_eose_received=1
+    NH->>Main: calls on_self_skill_eose_load_triggers callback
+    Main->>TM: trigger_manager_load_from_skills<br/>reads ALL cached skills via<br/>nostr_handler_get_self_events_by_kind_json
+    Note over TM: For each skill with trigger+filter tags:<br/>calls trigger_manager_add
+    Main->>Main: nostr_handler_wait_for_self_skill_eose returns 0
+    Main->>Main: Startup step 14 passes
+    Main->>Main: Enter main poll loop
+```
+
+### Path 2: Live skill event (post-startup)
+
+```mermaid
+sequenceDiagram
+    participant Relays as Nostr Relays
+    participant NH as nostr_handler
+    participant TM as trigger_manager
+
+    Note over NH: Subscription stays open after EOSE
+    Relays-->>NH: New/updated skill EVENT arrives
+    NH->>NH: on_self_skill_event
+    NH->>NH: register_trigger_from_self_skill_event
+    Note over NH: Checks: kind 31123/31124?<br/>Has trigger+filter tags?<br/>Is adopted via kind 10123?
+    NH->>TM: trigger_manager_add or update
+    NH->>NH: self_skill_cache_upsert_event_locked
+```
+
+### Path 3: Cron polling in main loop
+
+```mermaid
+sequenceDiagram
+    participant Main as main loop
+    participant TM as trigger_manager
+    participant Agent as agent.c
+
+    loop Every iteration
+        Main->>TM: trigger_manager_poll
+        Note over TM: Throttled to once per 30 seconds
+        TM->>TM: For each trigger where type==CRON:<br/>1. Validate cron_expr<br/>2. Check cron_matches_now<br/>3. Check last_cron_fire dedup - 50s guard
+        TM->>Agent: execute_llm_action with synthetic cron event
+    end
+```
+
+---
+
+## The Six Failure Points
+
+I have identified six places where a cron trigger can silently fail to load or fire. They are ordered from most likely to least likely given the logs from laantungir.net.
+
+### 1. EOSE timeout kills startup entirely
+
+**Where:** [`main.c:1494–1515`](src/main.c:1494)
+
+The agent waits 15 seconds for self-skill EOSE. If relays are slow or the connection is flaky, this times out and **the entire agent process exits**:
+
+```c
+const int self_skill_eose_timeout_ms = 15000;
+if (nostr_handler_wait_for_self_skill_eose(self_skill_eose_timeout_ms) != 0) {
+    // ... prints error, cleans up, return 1
+}
+```
+
+From [`debug.log`](debug.log) line 670:
+```
+[2026-04-06 16:16:49] [ERROR] startup checklist [14] Subscribe self-skill cache: failed
+    (self-skill EOSE not received within timeout)
+```
+
+**Impact:** If the agent crashes at startup, no triggers load at all. If systemd restarts it and it crashes again, you get a restart loop with zero cron execution.
+
+### 2. Adoption check gates live trigger registration
+
+**Where:** [`nostr_handler.c:1462`](src/nostr_handler.c:1462)
+
+When a skill event arrives live via [`on_self_skill_event()`](src/nostr_handler.c:2428), it calls [`register_trigger_from_self_skill_event()`](src/nostr_handler.c:1418) which checks:
+
+```c
+if (!self_skill_is_adopted_local(kind_val, pubkey->valuestring, d_tag)) {
+    DEBUG_INFO("live self-skill trigger ignored (not adopted) d_tag=%s", d_tag);
+    return;
+}
+```
+
+[`self_skill_is_adopted_local()`](src/nostr_handler.c:1366) scans `g_self_skill_events` for a kind 10123 event with an `["a", "31123:<pubkey>:<d_tag>"]` tag. If the adoption event hasn't arrived yet (race condition — skill event arrives before adoption event), the trigger is silently skipped.
+
+**Critically:** The bulk load path in [`trigger_manager_load_from_skills()`](src/trigger_manager.c:818) does **NOT** check adoption at all — it loads every skill with trigger+filter tags. So the adoption gate only affects the live path.
+
+### 3. Bulk load is one-shot with `loaded_once` guard
+
+**Where:** [`main.c:42`](src/main.c:42)
+
+```c
+if (ctx->loaded_once) {
+    DEBUG_TRACE("deferred trigger load skipped (already loaded once)");
+    return;
+}
+```
+
+The EOSE callback fires once, calls [`trigger_manager_load_from_skills()`](src/trigger_manager.c:818), sets `loaded_once = 1`, and never runs again. If a skill event arrives **after** EOSE but **before** the live path processes it, it falls into a gap:
+- The bulk load already ran and won't run again
+- The live [`register_trigger_from_self_skill_event()`](src/nostr_handler.c:1418) may reject it due to the adoption check
+
+### 4. Cron expression validation rejects silently at add time
+
+**Where:** [`trigger_manager.c:1106–1112`](src/trigger_manager.c:1106)
+
+```c
+if (t->trigger_type == TRIGGER_TYPE_CRON) {
+    if (!cron_expr_is_valid(filter_json, normalized_cron, sizeof(normalized_cron))) {
+        DEBUG_WARN("trigger add rejected: invalid cron expression d_tag=%s expr=%s", ...);
+        memset(t, 0, sizeof(*t));
+        return -1;
+    }
+}
+```
+
+This does log a warning, but the caller in [`trigger_manager_load_from_skills()`](src/trigger_manager.c:896) just silently skips to the next skill. The `considered` count increments but `loaded` does not — the only evidence is in the log line `trigger manager loaded X trigger(s) from self skills (considered=Y)` where X < Y.
+
+The existing plan in [`fix_cron_triggers_not_firing.md`](plans/fix_cron_triggers_not_firing.md) documents that a bare `*` was being used instead of `* * * * *`, and that shorthand expansion was added. This has been fixed.
+
+### 5. Poll throttle delays first evaluation by up to 30 seconds
+
+**Where:** [`trigger_manager.c:1395`](src/trigger_manager.c:1395)
+
+```c
+if (mgr->last_poll_at > 0 && (now - mgr->last_poll_at) < 30) {
+    return 0;
+}
+```
+
+After init, `last_poll_at` starts at 0 (fixed from the original bug where it was `time(NULL)`), so the first poll runs immediately. But subsequent polls are throttled to every 30 seconds. For a daily cron this is fine, but it means the cron match window is checked at most twice per minute.
+
+### 6. Cron dedup guard can skip legitimate fires
+
+**Where:** [`trigger_manager.c:1422`](src/trigger_manager.c:1422)
+
+```c
+if (t->last_cron_fire > 0 && (now - t->last_cron_fire) < 50) {
+    continue;
+}
+```
+
+With a 30-second poll interval and a 50-second dedup window, a cron that matches at minute X will fire once and then be suppressed for the next poll. This is correct behavior for preventing double-fires within the same minute. But if the system clock jumps or NTP adjusts, this could cause unexpected skips.
+
+---
+
+## Robustness Suggestions
+
+### A. Retry EOSE with backoff instead of hard abort
+
+**Current:** EOSE timeout → process exit.
+**Proposed:** Retry 2–3 times with increasing timeout (15s, 30s, 60s). If all retries fail, start the agent in degraded mode with only startup-config triggers active, and schedule a background re-attempt.
+
+```mermaid
+flowchart TD
+    SUB[Subscribe self-skills] --> WAIT{Wait for EOSE}
+    WAIT -->|Received| LOAD[Load triggers from skills]
+    WAIT -->|Timeout 15s| RETRY1{Retry 1 - 30s timeout}
+    RETRY1 -->|Received| LOAD
+    RETRY1 -->|Timeout| RETRY2{Retry 2 - 60s timeout}
+    RETRY2 -->|Received| LOAD
+    RETRY2 -->|Timeout| DEGRADED[Start in degraded mode<br/>startup triggers only<br/>schedule background retry]
+    LOAD --> READY[Agent READY]
+    DEGRADED --> READY
+```
+
+### B. Remove adoption gate from live trigger registration
+
+The bulk load path doesn't check adoption. The live path does. This inconsistency means a skill created via `skill_create` with `auto_adopt=true` might not register its trigger if the adoption event arrives on a different relay or with different timing.
+
+**Proposed:** Either:
+1. Remove the adoption check from [`register_trigger_from_self_skill_event()`](src/nostr_handler.c:1462) to match the bulk path, OR
+2. Add the adoption check to the bulk path too for consistency, but with a fallback: if adoption events haven't loaded yet, defer the check.
+
+Option 1 is simpler and more robust. The agent already only subscribes to its own pubkey's events, so all skills in the cache are self-authored.
+
+### C. Allow re-running bulk trigger load
+
+Remove the `loaded_once` guard or replace it with a debounced re-load. When new skill events arrive after EOSE, schedule a re-scan of all cached skills after a short delay (e.g., 5 seconds). This closes the gap between EOSE and late-arriving events.
+
+### D. Add a periodic trigger reconciliation
+
+Every N minutes (e.g., 5), compare the set of cached skills that have trigger+filter tags against the active trigger list. Register any missing triggers. This is a safety net that catches any trigger that was missed during startup.
+
+```c
+// In trigger_manager_poll, after cron evaluation:
+if (now - mgr->last_reconcile_at > 300) {
+    trigger_manager_load_from_skills(mgr);  // idempotent via update path
+    mgr->last_reconcile_at = now;
+}
+```
+
+### E. Log trigger registration summary at startup
+
+After the deferred trigger load, log not just the count but also which trigger types were loaded:
+
+```
+trigger manager loaded 3 trigger(s): dm=2 cron=1 webhook=0 chain=0 nostr-sub=0
+```
+
+This makes it immediately obvious from the log whether a cron trigger was picked up.
+
+### F. Add an HTTP API endpoint for trigger status
+
+Expose `/api/triggers` that returns the same JSON as the `trigger_list` tool. This allows external monitoring (e.g., a health check script) to verify that expected cron triggers are loaded without going through the LLM.
+
+---
+
+## Summary of What Happened on laantungir.net
+
+Based on the logs:
+
+1. The agent started successfully multiple times (startup step 14 passed with `skills=3 adoptions=1` or similar).
+2. The deferred trigger load status shows **only dm-type triggers** were loaded — no cron triggers appear in any log entry.
+3. On 2026-04-06, the agent failed at startup step 14 with EOSE timeout, meaning it never even got to trigger loading.
+4. There is **zero** evidence of `cron trigger matched` or `cron trigger skipped` in any log file, confirming the cron trigger was never in the active trigger set.
+
+The most likely explanation: the cron skill event exists on relays but either:
+- It was missing the `["trigger", "cron"]` and/or `["filter", "<expr>"]` tags when it was published
+- It was not adopted (no kind 10123 event referencing it) and arrived via the live path where adoption is checked
+- The cron expression was invalid and was silently rejected at add time
+- The EOSE timeout prevented the agent from ever reaching the trigger loading phase
+
+Running `trigger_list` on the live server will definitively answer which of these is the case.

plans/fix_self_skill_eose_race.md

@@ -0,0 +1,148 @@
+# Fix: Self-Skill Startup Race (step 14 false-negative)
+
+## Symptom
+
+`didactyl.service` / `simon.service` intermittently fail startup at step 14:
+
+```
+startup checklist [14] Subscribe self-skill cache: failed (no skill events found after EOSE)
+```
+
+…even though the required events (kind 31123/31124 skills and kind 10123 adoption list)
+demonstrably exist on `relay.laantungir.net` (verified with `nak`, returned in well under
+a second). On other restarts the identical setup succeeds: `ok (skills=3 adoptions=1)`.
+The failure is timing-dependent.
+
+## How startup relay polling works (mechanics)
+
+- Each startup step opens its **own** subscription (its own `REQ` + filter). Step 14's
+  filter is built in [`nostr_handler_subscribe_self_skills()`](src/nostr_handler.c:2800):
+  `{"kinds":[31123,31124,10123],"authors":[<agent_pubkey>],"limit":300}`.
+- That subscription is sent to **all** configured relays in parallel inside
+  [`nostr_relay_pool_subscribe()`](nostr_core_lib/nostr_core/core_relay_pool.c:967).
+- This is the **async/streaming** path: events arrive over time via
+  [`on_self_skill_event()`](src/nostr_handler.c:2478) which upserts into the shared cache
+  `g_self_skill_events`, and an EOSE-complete callback
+  ([`on_self_skill_eose`](src/nostr_handler.c:2066)) flips `g_self_skill_eose_received`.
+- Step 14 then immediately runs
+  [`nostr_handler_validate_self_skill_cache()`](src/nostr_handler.c:3089) against whatever
+  is in the cache at that instant.
+
+## Root cause
+
+The async EOSE-complete signal is decoupled from "did the relay that actually has the
+events get queried and deliver yet." Two independent contributing factors:
+
+1. **Relay connection timing.** The self-skill subscription is registered shortly after
+   startup. If `relay.laantungir.net` is not yet fully connected when the subscription's
+   completion is computed, the empty relays (`damus`, `primal`) EOSE almost instantly and
+   the per-relay **timeout fallback**
+   ([`core_relay_pool.c:2128`](nostr_core_lib/nostr_core/core_relay_pool.c:2128)) marks the
+   remaining relay "done" after `relay_timeout_seconds` (=12) without ever receiving its
+   events. EOSE-complete fires with an empty cache → validation fails.
+2. **Validation fires the instant completion is signaled**, with no re-check, so any race
+   where laantungir's events land microseconds later is lost.
+
+This matches the `<1s` `nak` observation: when laantungir is connected and queried, it
+answers almost instantly; the failures are the cycles where it wasn't
+connected/queried/processed before the async completion fired.
+
+### Why FIRST → FULL_SET alone does NOT fix it
+
+`maybe_complete_subscription_eose()` waits for **all** relays in both modes; the only
+difference is the payload passed to the callback. The cache is filled by the EVENT
+callback, not the EOSE payload. Changing the mode changes neither connection timing nor
+when events are available.
+
+## Fix: use the synchronous query for the startup self-skill load
+
+There is already a correct, synchronous "collect all events until EOSE/timeout, then
+return them" primitive used elsewhere at startup (e.g. kind-10002 discovery):
+
+- [`nostr_handler_query_json()`](src/nostr_handler.c:3395) →
+  [`nostr_relay_pool_query_sync()`](nostr_core_lib/nostr_core/core_relay_pool.c:1340).
+- A self-skill-specific wrapper already exists and reuses it:
+  [`nostr_handler_refresh_self_skill_cache_from_relays()`](src/nostr_handler.c:3751),
+  which queries kinds 31123/31124/10123 for the agent author (and also pulls adopted
+  skills), populating the cache synchronously.
+
+The synchronous query is the architecturally correct tool for "give me the complete
+current set before proceeding," which is exactly what step 14 needs. It also drives the
+poll/receive loop itself
+([`core_relay_pool.c:1405`](nostr_core_lib/nostr_core/core_relay_pool.c:1405)) until all
+connected relays EOSE or the timeout elapses.
+
+### Important caveat to handle: connection readiness
+
+`nostr_relay_pool_query_sync()` only queries relays that are **connected at call time**
+(`if (connected_count == 0) return NULL;` at
+[`core_relay_pool.c:1392`](nostr_core_lib/nostr_core/core_relay_pool.c:1392)). If
+`relay.laantungir.net` is still mid-connect when step 14 runs, a sync query could still
+miss it. Therefore the fix must ensure the relay holding the events is connected (or wait
+briefly for it) before/within the query.
+
+### Plan
+
+1. **Replace the step-14 async wait+validate with a synchronous load.** In
+   [`src/main.c`](src/main.c) step 14 (~line 1518), instead of relying solely on
+   `nostr_handler_wait_for_self_skill_eose()` + an immediate
+   `nostr_handler_validate_self_skill_cache()`:
+   - Keep registering the live subscription (so ongoing skill updates still stream in via
+     `on_self_skill_event`) — this is still wanted for runtime.
+   - For the startup *gate*, call
+     [`nostr_handler_refresh_self_skill_cache_from_relays(timeout_ms)`](src/nostr_handler.c:3751)
+     with a sensible timeout (e.g. 8000–10000 ms). This performs the synchronous,
+     connection-aware query and fills `g_self_skill_events`.
+   - Then run `nostr_handler_validate_self_skill_cache(&skills, &adoptions)`.
+
+2. **Wait for the self relay (laantungir) to be connected before the sync query.** Reuse
+   the existing relay-readiness helper pattern (`wait_for_connected_relays`) — but ensure
+   we wait specifically until the relay list discovered from kind 10002 (which includes
+   `relay.laantungir.net`) is connected, not just "any relay." If we already have a
+   connected-count wait, extend/bound it so the relay that owns the events has a fair
+   chance to connect before the sync query runs.
+
+3. **Bounded retry around the sync query.** If the first sync query returns an empty cache,
+   retry the sync query a small, bounded number of times (e.g. up to ~5–8s total),
+   pumping `nostr_handler_poll()` between attempts to let connections settle. Only fail
+   step 14 after the bounded retries still yield an empty cache. This converts a transient
+   connection-timing miss into a brief wait instead of a hard failure.
+
+4. **Keep the async subscription for runtime updates.** Do not remove the live
+   subscription; it's still responsible for picking up skill changes after startup. Only
+   the *startup gate* switches to the synchronous load for determinism.
+
+### Why this is the right layer
+
+- It uses the library's intended synchronous collect-all primitive rather than racing a
+  streaming subscription against an immediate validation.
+- It is connection-aware and bounded, so a slow/late relay connect becomes a short wait,
+  not a false "no skill events" failure.
+- It does not require modifying `nostr_core_lib` (though if desired, a follow-up could add
+  a `query_sync` variant that waits for a named relay to connect; not required here).
+
+## Interaction with the failure-DM throttle (already shipped)
+
+- On success, the READY path clears the throttle marker
+  ([`src/main.c`](src/main.c) `startup_failure_marker_clear`). No change needed.
+- After this fix, step-14 failures should be genuinely rare (real outage / events truly
+  absent), and the (single, throttled) failure DM will carry relay states + needed event
+  kinds for accurate diagnosis.
+
+## Verification
+
+1. Build (`make`) clean, then `build_static.sh`.
+2. Deploy to VM410; restart both services many times in a row and confirm step 14 reaches
+   `ok (skills=N adoptions=M)` **consistently** (no intermittent false negatives).
+3. Inspect logs to confirm the synchronous query path is used and that, on a cold cycle,
+   it waits for `relay.laantungir.net` to connect and then returns the events.
+4. Negative test: configure only empty relays (no skill events anywhere) and confirm step
+   14 still fails after the bounded retries (no false positive), sending exactly one
+   throttled failure DM.
+5. Confirm a normal successful startup still sends the startup DM and clears the marker.
+
+## Out of scope (possible follow-ups)
+
+- Adding a `nostr_core_lib` `query_sync` variant that explicitly waits for specific
+  relays to connect before issuing the REQ.
+- Softening step 14 into a degraded-start mode.

plans/fix_trigger_adoption_gate.md

@@ -0,0 +1,77 @@
+# Fix: Trigger Manager Bypasses Skill Adoption List
+
+## Problem
+
+`trigger_manager_load_from_skills()` and `trigger_manager_reconcile_from_relays()`
+activate cron/webhook/subscription triggers for **every** self-authored skill event
+(kind 31123/31124) that has trigger metadata, without checking whether the skill is
+on the kind 10123 adoption list.
+
+This means a skill that was published but never adopted (or was un-adopted) will
+still have its cron trigger firing.
+
+Contrast: `agent.c:refresh_adopted_skills_cache_if_needed()` properly fetches the
+kind 10123 list, parses `"a"` tags, and only loads adopted skills — and also checks
+the `enabled` tag. The trigger manager was written as a parallel system that skips
+both gates.
+
+## Root Cause
+
+- `trigger_manager.c:939` — `trigger_manager_load_from_skills()`: no reference to
+  kind 10123 or adoption anywhere in the function. Calls `trigger_manager_add()`
+  unconditionally.
+- `trigger_manager.c:592` — `trigger_manager_reconcile_from_relays()`: same bug.
+  Currently disabled (`enable_periodic_reconcile = 0` at line 1575) but should be
+  fixed before re-enabling.
+- Neither function checks the `enabled` tag either, unlike
+  `trigger_manager_load_from_startup_events()` (line 1078) which does check it.
+
+## Fix
+
+### 1. Add a static helper: `load_adopted_d_tags()`
+
+Add a static function in `trigger_manager.c` that:
+- Fetches kind 10123 events via `nostr_handler_get_self_events_by_kind_json(10123)`
+- Selects the latest event by `created_at` (same logic as agent.c)
+- Parses `"a"` tags using a local `parse_skill_address_tag_local()` equivalent
+- Populates a fixed-size array of adopted d_tag strings
+- Returns the count
+
+Since both call sites only deal with self-authored skills, matching on d_tag
+alone is sufficient (the pubkey in the "a" tag will be the agent's own).
+
+### 2. Add `enabled` tag check
+
+Both functions should read the `enabled` tag (defaulting to `"true"`) and skip
+skills where `enabled` is `false` or `0`, matching the pattern already used in
+`trigger_manager_load_from_startup_events()`.
+
+### 3. Gate `trigger_manager_load_from_skills()`
+
+Before calling `trigger_manager_add()`, check:
+1. The skill's d_tag is in the adopted set
+2. The skill's `enabled` tag is not false/0
+
+If the adoption list is empty or missing, log a warning and load nothing (do not
+fall back to loading all skills — that's the bug).
+
+### 4. Gate `trigger_manager_reconcile_from_relays()`
+
+Apply the same adoption + enabled checks. This ensures the code is correct when
+`enable_periodic_reconcile` is eventually flipped back to 1.
+
+### 5. Pass `is_enabled` to `trigger_manager_add()`
+
+Currently both functions pass `1` (hardcoded enabled) as the `enabled` parameter.
+Change to pass the actual `is_enabled` value derived from the `enabled` tag.
+
+## Files Changed
+
+- `src/trigger_manager.c` — add helper, fix both functions
+
+## Risk
+
+Low. The fix adds a filter before `trigger_manager_add()`. If the adoption list
+is present and correct, behavior is unchanged for adopted skills. If the adoption
+list is missing, triggers simply won't load (which is the correct behavior —
+nothing should fire if nothing is adopted).

plans/nip17_gift_wrap_investigation.md

@@ -0,0 +1,127 @@
+# NIP-17 Gift Wrap Send Failure — Investigation
+
+## Status: Resolved — Fixed in code (2026-04-11)
+
+## Date Discovered: 2026-04-11
+
+## Symptom
+
+Every outbound NIP-17 DM send from the Anvil agent fails with:
+```
+NIP-17 send aborted: gift_wrap creation failed for 1ec454734dcbf6fe...
+auto DM fallback to NIP-04 for 1ec454734dcbf6fe... after NIP-17 send failure
+```
+
+The agent successfully falls back to NIP-04 (kind 4), so DMs are still delivered. However, NIP-17 outbound is completely broken.
+
+**Inbound NIP-17 works fine** — the agent successfully receives and decrypts kind 1059 gift wraps from the admin.
+
+## Affected Code Path
+
+### Send path (broken):
+1. `nostr_handler_send_dm_auto_with_role()` in `src/nostr_handler.c:3193` — routes to NIP-17 when `dm_protocol` is `nip17` or `both`
+2. `nostr_handler_send_dm_nip17_with_role()` in `src/nostr_handler.c:4050` — creates chat event, calls `nostr_nip17_send_dm()`
+3. `nostr_nip17_send_dm()` in `nostr_core_lib/nostr_core/nip017.c:260` — iterates recipients, creates seal + gift wrap
+4. `nostr_nip59_create_seal()` in `nostr_core_lib/nostr_core/nip059.c:150` — **encrypts rumor JSON with NIP-44**
+5. `nostr_nip59_create_gift_wrap()` in `nostr_core_lib/nostr_core/nip059.c:226` — wraps seal with random key
+
+### Receive path (working):
+1. `on_event()` receives kind 1059
+2. `nostr_nip17_receive_dm()` in `nostr_core_lib/nostr_core/nip017.c:326` — unwraps gift, unseals rumor
+3. Successfully extracts kind 14 content
+
+## Probable Root Cause: Fixed Buffer Overflow in Seal Encryption
+
+In `nostr_core_lib/nostr_core/nip059.c:163-165`:
+
+```c
+char encrypted_content[4096]; // Should be large enough for most events
+int encrypt_result = nostr_nip44_encrypt(sender_private_key, recipient_public_key,
+                                        rumor_json, encrypted_content, sizeof(encrypted_content));
+```
+
+The seal creation uses a **fixed 4096-byte stack buffer** for the NIP-44 encrypted output. The rumor JSON includes the full DM message content. When the agent sends long responses (the FIPS mesh conversation had multi-KB markdown tables), the rumor JSON easily exceeds 4096 bytes after NIP-44 encryption overhead (base64 encoding roughly 4/3x expansion + padding + nonce).
+
+**Evidence:**
+- The agent's DM responses in the log were 2-5KB of markdown content
+- After JSON serialization of the kind 14 rumor (adding pubkey, tags, created_at, kind fields), the total is larger
+- NIP-44 encryption adds: 32-byte nonce + padding + base64 encoding → roughly 1.5-2x expansion
+- A 3KB message → ~4.5KB rumor JSON → ~6-9KB encrypted → overflows 4096 buffer
+- `nostr_nip44_encrypt()` returns error, `nostr_nip59_create_seal()` returns NULL
+- `nostr_nip17_send_dm()` skips the recipient, returns 0 wraps
+- `nostr_handler_send_dm_nip17_with_role()` logs "gift_wrap creation failed"
+
+**Why receive works:** The receive path uses `nostr_nip44_decrypt()` which likely allocates dynamically or has a larger buffer.
+
+## Secondary Suspect: NIP-44 Encryption Implementation
+
+The NIP-44 encrypt function itself may have issues with large payloads. Need to check:
+- `nostr_nip44_encrypt()` in `nostr_core_lib/nostr_core/nip044.c`
+- Whether it handles the output buffer size parameter correctly
+- Whether it returns an error code that distinguishes "buffer too small" from other failures
+
+## Anvil Config Context
+
+The Anvil agent's genesis config (`/home/user/anvil/genesis.jsonc`) has:
+```json
+"dm_protocol": "nip04"
+```
+
+But the encrypted user-settings on Nostr (kind 30078) may have overridden this to `"both"` at runtime, which is why NIP-17 send is being attempted.
+
+## Recommended Fix
+
+### Option A: Dynamic allocation (preferred)
+Replace the fixed 4096-byte buffer in `nostr_nip59_create_seal()` with dynamic allocation:
+```c
+size_t rumor_len = strlen(rumor_json);
+size_t encrypted_buf_size = rumor_len * 2 + 256; // generous overhead for NIP-44
+char* encrypted_content = malloc(encrypted_buf_size);
+```
+
+### Option B: Larger fixed buffer (quick fix)
+Increase the buffer to 64KB or 128KB:
+```c
+char encrypted_content[131072]; // 128KB should handle any reasonable DM
+```
+Note: This is a stack allocation, so very large buffers could cause stack overflow.
+
+### Also check `nostr_nip59_create_gift_wrap()`
+The gift wrap function at `nip059.c:226` may have a similar fixed-buffer issue for encrypting the seal JSON.
+
+## Log Evidence
+
+From `/home/user/anvil/debug.log` (2026-04-11):
+
+```
+[2026-04-11 09:45:14] [WARN ] NIP-17 send aborted: gift_wrap creation failed for 1ec454734dcbf6fe...
+[2026-04-11 09:45:14] [WARN ] auto DM fallback to NIP-04 for 1ec454734dcbf6fe... after NIP-17 send failure
+[2026-04-11 09:50:16] [WARN ] NIP-17 send aborted: gift_wrap creation failed for 1ec454734dcbf6fe...
+[2026-04-11 09:50:16] [WARN ] auto DM fallback to NIP-04 for 1ec454734dcbf6fe... after NIP-17 send failure
+[2026-04-11 09:53:42] [WARN ] NIP-17 send aborted: gift_wrap creation failed for 1ec454734dcbf6fe...
+[2026-04-11 09:53:42] [WARN ] auto DM fallback to NIP-04 for 1ec454734dcbf6fe... after NIP-17 send failure
+```
+
+This pattern is 100% consistent — every outbound NIP-17 attempt fails, every time.
+
+## Related Files
+
+- `nostr_core_lib/nostr_core/nip059.c` — Gift wrap / seal creation (probable bug location)
+- `nostr_core_lib/nostr_core/nip044.c` — NIP-44 encryption (check buffer handling)
+- `nostr_core_lib/nostr_core/nip017.c` — NIP-17 DM send/receive orchestration
+- `src/nostr_handler.c:4050` — Agent-level NIP-17 send function
+- `plans/nip17_messaging.md` — Original NIP-17 implementation plan
+
+## Related Existing Plan
+
+The `plans/nip17_messaging.md` document covers the original NIP-17 implementation. This investigation is specifically about the send-side gift wrap failure that emerged in production.
+
+## Resolution Summary
+
+Implemented in `nostr_core_lib/nostr_core/nip059.c`:
+
+- Replaced fixed encryption buffers in `nostr_nip59_create_seal()` and `nostr_nip59_create_gift_wrap()` with dynamically sized heap buffers calculated from NIP-44 padding/base64 overhead.
+- Replaced fixed decrypt buffers in `nostr_nip59_unwrap_gift()` and `nostr_nip59_unseal_rumor()` with dynamic buffers sized from ciphertext length.
+- Added missing cleanup path in `nostr_nip59_create_seal()` for failure after encryption allocation.
+
+Expected outcome: outbound NIP-17 gift wrap creation no longer fails for multi-KB DM payloads due to fixed buffer limits.

plans/nsigner_integration.md

@@ -0,0 +1,440 @@
+# n_signer Integration Plan — didactyl
+
+## Goal
+
+Separate control of the nsec from the didactyl agent by routing signing/encryption
+through `n_signer` — a separate foreground process that holds key material in locked
+memory and signs on request. A later phase may embed n_signer into the didactyl binary
+so one self-contained binary spawns an n_signer in a separate window; that is deferred
+because of a reliability concern (if the agent loses signing ability it cannot even DM
+its admin about the failure).
+
+This plan covers two distinct work items:
+
+1. **Update didactyl's vendored `nostr_core_lib`** to the upstream version that already
+   implements the nsigner client (M1–M6 complete, upstream `VERSION` 0.6.6). This is a
+   mechanical sync that changes no runtime behavior.
+2. **Opt-in migration of didactyl call sites** to the `nostr_signer_t` provider so the
+   raw private key can leave the agent process. This is the actual nsec-separation work
+   and is staged so reliability is preserved.
+
+---
+
+## Background — what upstream already provides
+
+Upstream `nostr_core_lib` (git.laantungir.net/nostr_core_lib, v0.6.6) has shipped the
+full signer abstraction. didactyl's vendored copy predates all of it.
+
+New upstream modules:
+
+- [`nostr_core/nostr_signer.{h,c}`](../nostr_core_lib/nostr_core/nostr_signer.h) —
+  `nostr_signer_t` opaque handle + vtable. Two backends:
+  - **local** — `nostr_signer_local(privkey[32])`, wraps today's raw-key path. Output-equivalent.
+  - **remote (nsigner)** — `nostr_signer_nsigner_unix/serial/tcp/fds(...)`, guarded by
+    `NOSTR_ENABLE_NSIGNER_CLIENT`.
+- [`nostr_core/nsigner_client.{h,c}`](../nostr_core_lib/nostr_core/nsigner_client.h) —
+  framing, JSON-RPC verbs, kind-27235 auth envelope, error mapping.
+- [`nostr_core/nsigner_transport.{h,c}`](../nostr_core_lib/nostr_core/nsigner_transport.h) —
+  pluggable transport vtable: AF_UNIX abstract, TCP, USB-CDC serial, fd-pair (stdio/qrexec).
+
+Verbs mirror n_signer's wire contract: `get_public_key`, `sign_event`,
+`nip04_encrypt/decrypt`, `nip44_encrypt/decrypt`.
+
+Parallel `*_with_signer` entry points added across the library (legacy raw-key APIs are
+preserved as thin wrappers over the local backend, so existing projects keep compiling
+and behaving identically):
+
+- NIP-01: `nostr_create_and_sign_event_with_signer`
+- NIP-17: `nostr_nip17_create_relay_list_event_with_signer`,
+  `nostr_nip17_send_dm_with_signer`, `nostr_nip17_receive_dm_with_signer`
+- NIP-42: `nostr_nip42_create_auth_event_with_signer`
+- NIP-46: request/response/decrypt/session-init `*_with_signer` variants
+- NIP-59: seal/unwrap/unseal `*_with_signer` variants
+- NIP-60 / NIP-61: all cashu event-creation `*_with_signer` variants
+- Blossom: `blossom_create_auth_header_with_signer`,
+  `blossom_upload_with_signer`, `blossom_upload_file_with_signer`,
+  `blossom_delete_with_signer`
+- Relay pool: `nostr_relay_pool_set_auth_with_signer` — the pool now stores an
+  `auth_signer` instead of a raw key, so NIP-42 AUTH events are signed through the
+  provider on relay challenge. **This was the hardest blocker and it is already solved
+  upstream.**
+
+Upstream `build.sh` unconditionally defines `-DNOSTR_ENABLE_NSIGNER_CLIENT=1` and
+compiles `nostr_signer.c`, `nsigner_transport.c`, `nsigner_client.c`.
+
+Dependency direction is unchanged and non-circular: n_signer (server) depends on
+`nostr_core_lib` for leaf crypto; `nostr_core_lib` gains a *client* that consumes its
+own primitives. Nobody imports anyone's binary in a loop.
+
+---
+
+## Current didactyl state (what we are updating from)
+
+- `nostr_core_lib/` is a **vendored source directory** (no git submodule; no
+  `.gitmodules`). Built via `./nostr_core_lib/build.sh --nips=001,004,...,061` into a
+  static `libnostr_core_*.a`, linked by [`Makefile`](../Makefile:56) and the Docker
+  static build ([`Dockerfile.alpine-musl`](../Dockerfile.alpine-musl:81)).
+- The vendored tree has **none** of the nsigner pieces: no `nostr_signer.*`,
+  no `nsigner_*.*`, no `*_with_signer` variants. The relay pool still uses the raw-key
+  AUTH path ([`nostr_core_lib/nostr_core/core_relay_pool.c`](../nostr_core_lib/nostr_core/core_relay_pool.c:682)).
+- didactyl holds the raw 32-byte key in [`cfg->keys.private_key`](../src/config.h:16)
+  and passes it directly into ~30+ library call sites (event signing, NIP-04/44
+  encrypt/decrypt, NIP-17 gift wraps, NIP-60/61 cashu, blossom, relay pool AUTH).
+
+---
+
+## Architecture (target)
+
+```mermaid
+graph TD
+    A[didactyl src] --> B[nostr_core_lib vendored]
+    B --> C[nostr_signer_t local backend]
+    B --> D[nostr_signer_t nsigner remote backend]
+    D --> E[nsigner client: framing + auth envelope]
+    E --> F[nostr_create_and_sign_event in nostr_core_lib]
+    G[n_signer server binary] --> B
+```
+
+didactyl constructs **one** `nostr_signer_t*` at startup and threads it through every
+signing/encryption/AUTH call site. The backend is chosen by config:
+
+- `signer.mode = "local"` → `nostr_signer_local(cfg->keys.private_key)` (today's behavior).
+- `signer.mode = "nsigner_unix"` → `nostr_signer_nsigner_unix(socket_name, role, timeout_ms)`.
+- (future) `nsigner_tcp`, `nsigner_serial`, `nsigner_fds`.
+
+The raw `cfg->keys.private_key` is only populated in `local` mode. In remote modes the
+agent process never holds the nsec; it learns its own pubkey via
+`nostr_signer_get_public_key()`.
+
+---
+
+## Phasing
+
+### Phase 1 — Update vendored nostr_core_lib (mechanical, zero behavior change)
+
+Goal: bring didactyl's `nostr_core_lib` source tree to upstream v0.6.6 so the signer
+abstraction and nsigner client are available. **No didactyl source changes.** Existing
+raw-privkey APIs are preserved upstream as thin wrappers over the local backend, so all
+~30 call sites keep compiling and behaving identically.
+
+Steps:
+
+1. Snapshot current vendored tree for diffing/rollback:
+   `cp -a nostr_core_lib nostr_core_lib.old`
+2. Replace the vendored source tree with upstream v0.6.6. Preferred: copy the upstream
+   `nostr_core/`, `cjson/`, `nostr_websocket/`, `platform/`, `build.sh`, `CMakeLists.txt`
+   into `nostr_core_lib/`, preserving didactyl-local build quirks only if any exist
+   (none found — the Dockerfile already `sed`s `build.sh` in-place for fortification).
+   Do **not** carry over upstream's prebuilt `.a`/`.o` files, `pool.log`, `.venv*`,
+   `backups/`, `verify_*` artifacts — match didactyl's existing `.gitignore` hygiene.
+3. Rebuild the static library:
+   `cd nostr_core_lib && ./build.sh --nips=001,004,005,006,011,013,017,019,021,042,044,046,059,060,061`
+   (same NIP set as today; `nostr_signer.c` / `nsigner_*.c` are compiled unconditionally
+   by upstream `build.sh`).
+4. Rebuild didactyl: `make clean && make`. Confirm it compiles and links with no source
+   changes.
+5. Smoke test: run the agent with an nsec-only config and confirm signing/DMs/relay AUTH
+   still work byte-for-byte (the upstream local backend is output-equivalent to the
+   legacy path; there is an upstream test `test_event_creation_equivalence_with_signer`
+   that asserts this).
+6. Static (Docker) build: `./build_static.sh`. The Dockerfile copies `nostr_core_lib/`
+   and runs `./build.sh --nips=all`; verify the static binary still builds and runs.
+7. Record the upstream version pinned in this repo (e.g. a one-line
+   `nostr_core_lib/UPSTREAM_VERSION` file = `0.6.6`) so future syncs are auditable.
+
+Exit criteria: didactyl builds and runs identically, but now links a `nostr_core_lib`
+that exposes `nostr_signer_t` and the nsigner client. No nsec separation yet.
+
+### Phase 2 — Signer provider in didactyl config + startup (local backend, still no separation)
+
+Goal: introduce a `nostr_signer_t*` in didactyl constructed at startup, backed by
+`local` mode by default. This is the seam; behavior is still identical.
+
+#### 2a. Config schema
+
+[`src/config.c`](../src/config.c) / [`src/config.h`](../src/config.h): add a `signer`
+block (sibling of `keys`):
+
+```jsonc
+"signer": {
+  "mode": "local",            // "local" | "nsigner_unix" | (future) "nsigner_tcp" | "nsigner_serial" | "nsigner_fds"
+  "socket_name": "",          // nsigner_unix: abstract socket name (without @); empty = auto-discover single running signer
+  "role": "main",             // n_signer role selector
+  "timeout_ms": 15000,
+  "auth_privkey_hex": ""      // optional, for TCP auth envelope only
+}
+```
+
+Default `mode = "local"`. Backward compatible: if `signer` block is absent, behave as
+`local` using `keys.nsec`. Validation: in any `nsigner_*` mode, `keys.nsec` is optional
+and ignored (the agent learns its pubkey from the signer); in `local` mode `keys.nsec`
+remains required.
+
+#### 2b. User-facing surfaces (how the operator chooses n_signer)
+
+didactyl has three startup surfaces today; the n_signer choice is exposed on all three,
+consistent with existing patterns:
+
+**1. Interactive setup wizard** ([`src/setup_wizard.c`](../src/setup_wizard.c),
+`new_agent_identity_step` at line ~2116). Today the Identity page offers:
+`[g]enerate new keypair` / `[p]rovide existing nsec`. Add a third option:
+
+- `[s]ign with a running n_signer (separate the nsec from the agent)`
+
+When chosen, the wizard:
+- Does **not** prompt for an nsec. Instead prompts for:
+  - socket name (default: auto-discover the single running signer),
+  - role (default `main`),
+  - timeout (default 15000ms).
+- Performs a live `nostr_signer_nsigner_unix(...)` + `nostr_signer_get_public_key()`
+  connectivity check immediately, so the operator gets confirmation ("Connected to
+  n_signer @nsigner_hairy_dog; agent npub: npub1...") before proceeding.
+- Writes `signer.mode = "nsigner_unix"` (plus socket_name/role/timeout) into the
+  generated genesis JSONC and **omits** `keys.nsec`.
+- The existing `[p]rovide existing nsec` path stays as `local` mode (the default).
+
+This keeps the trust model visible at the moment the operator commits to an identity:
+either the nsec lives in the agent (`local`) or it does not (`nsigner_unix`).
+
+**2. CLI flags + env** ([`src/main.c`](../src/main.c) `print_usage` at line ~141 and
+arg parsing at line ~1233). Add:
+
+- `--signer <mode>` — one of `local`, `nsigner_unix`, `nsigner_tcp`, `nsigner_serial`,
+  `nsigner_fds`. Overrides `signer.mode` in config.
+- `--signer-socket <name>` — abstract socket name (nsigner_unix).
+- `--signer-role <role>` — n_signer role selector (default `main`).
+- `--signer-timeout <ms>` — per-call timeout (default 15000).
+- `--signer-tcp <host:port>` — shorthand for `--signer nsigner_tcp` + host/port.
+- `DIDACTYL_SIGNER` env — fallback for `--signer` (mirrors the `DIDACTYL_NSEC` pattern).
+
+When `--signer nsigner_unix` (or `DIDACTYL_SIGNER=nsigner_unix`) is set, `--nsec` /
+`DIDACTYL_NSEC` are not required and are ignored if present. This enables headless /
+systemd deployment where the nsec never touches the agent's argv or environment.
+
+Update `print_usage` examples to show the n_signer path, e.g.:
+`%s --signer nsigner_unix --signer-socket nsigner_hairy_dog --admin npub1...`
+
+**3. Genesis JSONC config** — the `signer` block in 2a is the canonical, persistent
+form. The wizard writes it; CLI flags override it for a single run; env vars are the
+last fallback. This matches how `keys.nsec` / `--nsec` / `DIDACTYL_NSEC` already layer.
+
+Precedence (highest to lowest): CLI flag → env var → genesis `signer` block → default
+`local`. Same precedence as the existing key/admin overrides.
+
+#### 2c. Startup construction
+
+[`src/main.c`](../src/main.c): after loading config + applying CLI/env overrides,
+construct a single `nostr_signer_t* g_signer`:
+
+- `local` → `nostr_signer_local(cfg->keys.private_key)`.
+- `nsigner_unix` → `nostr_signer_nsigner_unix(socket_name, role, timeout_ms)`.
+- (future) `nsigner_tcp` / `nsigner_serial` / `nsigner_fds` analogously.
+
+Then derive the agent pubkey via `nostr_signer_get_public_key(g_signer, ...)` instead of
+`nostr_ec_public_key_from_private_key(cfg->keys.private_key, ...)`. In `local` mode this
+yields the same bytes; in remote mode it is the first n_signer round-trip and **doubles
+as the mandatory startup connectivity check** (Phase 4): failure here is fatal and loud.
+
+Hold `g_signer` alongside `g_cfg` / `g_pool` for the process lifetime; free on shutdown.
+
+Exit criteria: didactyl runs with a `nostr_signer_t*` in `local` mode by default, and
+the operator can choose `nsigner_unix` via wizard, CLI, or config. No call sites migrated
+yet (Phase 3). This is a safe, reviewable checkpoint — in `local` mode behavior is
+identical; in `nsigner_unix` mode the agent starts but signing still uses the local path
+until Phase 3 lands (so Phase 2 remote mode is a connectivity proof, not full separation).
+
+### Phase 3 — Migrate call sites to `*_with_signer` (enables real separation)
+
+Goal: route every signing/encryption/AUTH operation through `g_signer`. In `local` mode
+this is still output-equivalent; in `nsigner_unix` mode the nsec is no longer in the
+agent process.
+
+Migrate in this order (highest value / lowest risk first):
+
+1. **Relay pool AUTH** — replace
+   `nostr_relay_pool_set_auth(g_pool, g_cfg->keys.private_key, 1)` with
+   `nostr_relay_pool_set_auth_with_signer(g_pool, g_signer, 1)`. This is the single
+   change that delegates the deep-event-loop AUTH signing.
+2. **Event signing** — `nostr_create_and_sign_event(...)` →
+   `nostr_create_and_sign_event_with_signer(...)` at all sites (posts, kind 30078
+   config publish, startup events, etc.). Search: `nostr_create_and_sign_event` in
+   `src/`.
+3. **NIP-44 encrypt/decrypt** — the DM/memory/task/config/block-list sites. These call
+   `nostr_nip44_encrypt/decrypt(cfg->keys.private_key, peer, ...)`. Replace with
+   `nostr_signer_nip44_encrypt/decrypt(g_signer, peer_hex, ...)`. Note the signer API
+   takes hex pubkeys and returns heap strings via `char**` out-params, so each call site
+   needs a small adaptation (hex-encode the peer key, free the out-string).
+4. **NIP-04 encrypt/decrypt** — same pattern as NIP-44 for the legacy NIP-04 DM sites.
+5. **NIP-17 gift wraps** — `nostr_nip17_send_dm` / `nostr_nip17_receive_dm` →
+   `*_with_signer`. (The seal is signed with the agent key via the signer; the gift-wrap
+   ephemeral key stays local — that is correct and does not leak the nsec.)
+6. **NIP-60/61 cashu** — `nostr_nip60_create_*_event` / `nostr_nip61_create_*_event` →
+   `*_with_signer` in [`src/cashu_wallet.c`](../src/cashu_wallet.c).
+7. **Blossom** — `blossom_create_auth_header` / `blossom_upload` / `blossom_delete` →
+   `*_with_signer` in [`src/tools/tool_blossom.c`](../src/tools/tool_blossom.c).
+
+After each group, build + smoke test in `local` mode (output-equivalent) before
+testing in `nsigner_unix` mode against a running `n_signer`.
+
+Exit criteria: every signing/encryption/AUTH op flows through `g_signer`. With
+`signer.mode = "nsigner_unix"`, the agent process holds no nsec.
+
+### Phase 4 — Reliability & failure handling (critical, do before enabling remote by default)
+
+The user's stated concern: if the agent loses signing ability, it cannot even DM its
+admin about the failure. This must be addressed before remote mode is anything but
+opt-in.
+
+Design:
+
+- **Startup connectivity check is mandatory.** `nostr_signer_get_public_key()` is called
+  at startup for every mode. In remote mode, failure here is fatal and loud (agent
+  refuses to start, prints a clear error). Better to fail to start than to start unable
+  to sign.
+- **Runtime signing failure** — classify by error:
+  - `approval_denied` / `policy_denied` / `unknown_role` → not a transient error; surface
+    to agent log and admin context, do not retry blindly.
+  - transport/IO error (n_signer crashed, socket gone) → the nsigner transport has a
+    `reconnect` hook; the client retries once with reconnect, then returns an error.
+- **Admin notification path.** Because DMs themselves require signing, a signing outage
+  is a catch-22 for "DM the admin". Mitigations, in order of preference:
+  1. **Health-gate before sending.** Before attempting an admin DM, do a cheap
+     `nostr_signer_get_public_key()` ping. If it fails, fall back to a **local,
+     keyless** notification channel: stderr/log + HTTP API health endpoint
+     ([`src/http_api.c`](../src/http_api.c)) exposes a `signer_unhealthy` flag. The admin
+     monitors the HTTP health endpoint (or process supervisor) rather than relying on a
+     DM that requires the broken signer.
+  2. **Optional emergency local key.** A config-gated `signer.emergency_local_nsec`
+     used *only* to sign admin DMs when the remote signer is unreachable. This is a
+     deliberate policy tradeoff (it re-introduces a key in-process, scoped to admin
+     alerts only) and should be off by default. Document the tradeoff clearly.
+  3. **Process supervisor.** systemd/`didactyl` service restarts on signer health
+     failure; the supervisor's logs are the out-of-band channel.
+- **Recommendation for v1:** ship (1) + (3). Leave (2) as a documented opt-in for
+  operators who prioritize alert delivery over strict key separation. This keeps the
+  default trust model clean while making the failure observable out-of-band.
+
+Exit criteria: a signing outage is detectable out-of-band (HTTP health + logs +
+supervisor), and the agent does not silently hang. Remote mode is still opt-in.
+
+#### Phase 4 implementation status (items 18–20) — COMPLETE
+
+Items 18, 19, and 20 are implemented as follows. Behavior is backward compatible
+and remote mode remains opt-in.
+
+**Item 18 — Runtime signer health classification & tracking**
+
+- New module [`src/signer_health.{h,c}`](../src/signer_health.h) holds a
+  process-global, mutex-protected health state: `unknown | healthy | unhealthy`,
+  the configured signer mode snapshot, the last error reason string, and the
+  last error / last ok unix timestamps.
+- [`src/main.c`](../src/main.c) `construct_signer()` records the mode at startup
+  and records `ok` on a successful connectivity check (`get_public_key`) or
+  `failure` (with the nostr error code) on construction/connectivity failure.
+  The fatal+loud startup behavior is preserved; error messages now explicitly
+  include `mode=`, `socket=`, `role=`, `timeout_ms=`, and `rc=` so the operator
+  knows exactly which signer context failed.
+- The migrated signer call paths in [`src/nostr_handler.c`](../src/nostr_handler.c)
+  (NIP-44 self encrypt/decrypt, NIP-04 incoming DM decrypt, NIP-04 outgoing DM
+  encrypt) call `signer_health_record_ok()` on success and
+  `signer_health_record_failure(rc, "<verb>")` on failure. Classification maps
+  nostr error codes to short labels: `transport/IO` (IO/network), `crypto/auth`,
+  `resource`, `invalid-input`, `unknown`. This is deliberately minimal — no broad
+  rewrite of the tool/agent/cashu/block-list signer sites; the central DM and
+  self-config paths are instrumented, which is where an outage first surfaces.
+
+**Item 19 — Out-of-band health surface (HTTP + logs + supervisor)**
+
+- [`src/http_api.c`](../src/http_api.c) `handle_status()` (the `GET /api/status`
+  endpoint) now adds the following fields to the JSON response:
+  - `signer_mode` — the configured signer mode (`local` / `nsigner_unix` / `nsigner_tcp`).
+  - `signer_healthy` — `"true"` / `"false"` / `"unknown"`.
+  - `signer_health_state` — `healthy` / `unhealthy` / `unknown`.
+  - `signer_last_error` — human-readable `<classification>: <detail> (rc=<n>)`, or `""`.
+  - `signer_last_error_ts` — unix timestamp of the last unhealthy transition, or `null`.
+  - `signer_last_ok_ts` — unix timestamp of the last healthy observation, or `null`.
+  An operator (or supervisor / monitoring agent) can poll `/api/status` to detect a
+  signing outage without requiring a signed admin DM to come back.
+- `signer_health_record_failure()` and `signer_health_record_ok()` each emit a
+  one-line stderr warning on a health **transition** (healthy -> unhealthy, or
+  unhealthy -> healthy), including the mode and reason. Repeated failures within
+  the same unhealthy state do not spam the log.
+
+**Item 20 — Optional `emergency_local_nsec` (admin-DM delivery tradeoff)**
+
+- New config field `signer.emergency_local_nsec` (string, empty default) in
+  [`src/config.h`](../src/config.h) `signer_config_t`, parsed in
+  [`src/config.c`](../src/config.c) `parse_signer_config()`.
+- **No active fallback behavior is wired yet.** The field is parsed, stored, and
+  documented only — a feature-flag/placeholder so operators can pre-stage the
+  value. The actual "sign a minimal admin-alert DM with the emergency key when
+  the remote signer is unreachable" path is deferred until the Phase 4 health
+  surface (item 19) is proven in production.
+- **Tradeoff (documented here and in the config header comment):** off by default.
+  When eventually enabled, it reintroduces the nsec into the agent process
+  *only* for admin-alert fallback DMs. This is a deliberate operator-accepted
+  tradeoff: better to leak the nsec briefly to notify the admin than to fail
+  silently. Operators who prioritize strict key separation leave it empty and
+  rely on the HTTP health endpoint + supervisor logs (item 19) as the
+  out-of-band alert channel.
+
+**Validation**
+
+- `make clean && make` builds cleanly with the new `signer_health.c` source.
+- `./didactyl --help` and `./didactyl --version` unchanged in surface.
+- `GET /api/status` in local mode returns the new `signer_mode` / `signer_healthy`
+  / `signer_health_state` / `signer_last_error` / `signer_last_error_ts` /
+  `signer_last_ok_ts` fields (local mode reports `signer_healthy=true` after the
+  startup connectivity check).
+
+### Phase 5 (deferred) — Embedded n_signer spawn
+
+Goal: one self-contained didactyl binary that spawns an n_signer in a separate window
+at startup, for operators who want key separation without running a second process
+manually.
+
+Deferred because of the reliability concern above and because it couples didactyl's
+process model to n_signer's TUI/terminal-attached trust model. Revisit after Phase 4's
+health/observability story is proven in production with an external n_signer.
+
+Sketch (not for this round): didactyl forks `n_signer --mnemonic-fd N --socket-name <pinned>`
+in a new terminal (xterm/foot/etc.), passes the mnemonic over a pipe fd, pins the
+abstract socket name, and constructs `nostr_signer_nsigner_unix(<pinned name>, ...)`.
+The pinned socket name avoids discovery races. The trust anchor is still the
+terminal-attached n_signer process; didactyl is just a supervised spawner.
+
+---
+
+## Open decisions (resolved)
+
+1. **Where does the abstraction live?** Inside `nostr_core_lib`. It is the single
+   chokepoint, it solves the relay-AUTH blocker, and it is reusable. ✓ (already done
+   upstream)
+2. **How is the n_signer client code sourced into nostr_core_lib?** Already decided
+   upstream: the client (framing + auth envelope + transports) lives in
+   `nostr_core_lib` itself, guarded by `NOSTR_ENABLE_NSIGNER_CLIENT`. No vendoring of
+   n_signer's repo into nostr_core_lib; n_signer keeps depending on nostr_core_lib for
+   leaf crypto. ✓
+3. **Runtime failure handling.** See Phase 4: out-of-band health (HTTP + logs +
+   supervisor) by default; optional emergency-local-nsec as documented opt-in. ✓
+
+---
+
+## Risks & notes
+
+- **NIP set in `Makefile` vs `build.sh --nips=all` in Dockerfile.** Both must include
+  the NIPs didactyl uses. The signer core (`nostr_signer.c`, `nsigner_*.c`) is compiled
+  unconditionally by upstream `build.sh`, so the nsigner client is available in both
+  build paths. Verify after sync.
+- **Static link footprint.** nsigner client + transports add a small amount of object
+  code (unix/tcp/serial/fd transports). Negligible vs. the existing websocket/curl/openssl
+  surface. Serial transport pulls in `<termios.h>` — already POSIX, fine for musl.
+- **Output equivalence.** Upstream's local backend is asserted equivalent by
+  `test_event_creation_equivalence_with_signer`. Phase 1 smoke test should still
+  verify a known event signs to the same id as before.
+- **`cfg->keys.private_key` lifetime.** In remote mode this buffer is zeroed/unused.
+  Keep the field for `local` mode and for the optional emergency key; do not remove it.
+- **Hex pubkey plumbing.** The signer's encrypt/decrypt verbs take hex pubkeys and
+  return heap strings. Several didactyl sites currently pass raw 32-byte keys. Each
+  migrated site needs a small hex-encode + free adaptation. Mechanical but touches
+  many files — Phase 3 step 3/4 is the bulk of the work.

plans/remove_dead_dm_history_helpers.md

@@ -0,0 +1,58 @@
+# Remove Dead DM-History Helper Functions in `agent.c`
+
+## Background
+
+While investigating how Didactyl maintains continuity across a DM "chat session", two functions in [`src/agent.c`](../src/agent.c) were found to be compiled-but-unreferenced, marked with `__attribute__((unused))` to suppress compiler warnings:
+
+- [`append_recent_admin_dm_history`](../src/agent.c:1065)
+- [`build_recent_admin_dm_history_messages`](../src/agent.c:1800) (wraps the above)
+
+These were part of an older design where the agent automatically injected the last N admin DM turns into every LLM call. The current architecture is **skill-driven**: DM history only reaches the LLM when an adopted, triggered skill explicitly pulls it in via the `{{dm_history}}` / `{{nostr_dm_history(...)}}` template variables or the `nostr_dm_history` tool (see [`tool_agent.c`](../src/tools/tool_agent.c:284) and [`tools_schema.c`](../src/tools/tools_schema.c:1606)). The dead functions are now a source of confusion for anyone reading the code to understand chat-session behavior.
+
+## Goal
+
+Remove the dead functions and any symbols used exclusively by them, without changing runtime behavior.
+
+## Scope Analysis (verified before planning)
+
+A repo-wide search for each symbol confirmed the following:
+
+| Symbol | Only callers | Disposition |
+|---|---|---|
+| [`append_recent_admin_dm_history`](../src/agent.c:1065) | called by `build_recent_admin_dm_history_messages` (also dead) | **delete** |
+| [`build_recent_admin_dm_history_messages`](../src/agent.c:1800) | no callers | **delete** |
+| [`AGENT_HISTORY_TURNS`](../src/agent.c:38) | referenced only inside the dead `append_recent_admin_dm_history` | **delete** |
+| [`AGENT_HISTORY_QUERY_LIMIT`](../src/agent.c:39) | defined but zero references repo-wide | **delete** |
+| [`append_simple_message`](../src/agent.c:187) | many live callers throughout `agent.c` | **keep** |
+| [`nostr_handler_get_dm_history_json`](../src/nostr_handler.c:4384) | live via [`tool_agent.c`](../src/tools/tool_agent.c:318) | **keep** |
+
+No non-source references (Makefile, tests, docs) depend on these symbols.
+
+## Risks
+
+Very low. Both functions carry `__attribute__((unused))` so they are not linked into any runtime path. The only failure modes are accidental deletion of something still live, which the scope analysis above rules out.
+
+## Verification Strategy
+
+1. Clean build with `make` — must succeed with no new warnings.
+2. Existing tests under [`tests/`](../tests/) pass (`python tests/run_tests.py` or the project's usual invocation).
+3. Manual sanity check: start an agent, send a DM, confirm normal reply — no regression, since the deleted code was never on the hot path.
+
+## Mermaid: before/after
+
+```mermaid
+flowchart LR
+    subgraph Before
+        A1[agent.c dead funcs] -. unused attr .- B1[compiler silences warning]
+        A1 --> C1[reader assumes auto DM history replay]
+        C1 --> D1[confusion about session behavior]
+    end
+    subgraph After
+        A2[agent.c clean] --> E2[skill-driven history only]
+        E2 --> F2[intent matches code]
+    end
+```
+
+## Follow-on (out of scope for this change)
+
+The documentation in [`docs/CONTEXT.md`](../docs/CONTEXT.md) already describes the skill-driven assembly model correctly, but neither that file nor [`docs/SKILLS.md`](../docs/SKILLS.md) explicitly states "DM history is not automatic — it only appears when a skill references it." A brief clarifying paragraph could be added in a separate change.

plans/startup_failure_admin_dm.md

@@ -0,0 +1,285 @@
+# Startup Failure Admin DM Notification
+
+> **STATUS UPDATE (follow-up phase):** The base feature (send a failure DM) is
+> implemented and verified on VM410. However, because the failure happens inside the
+> systemd `Restart=on-failure` loop (`RestartSec=10`), the admin now receives a *new*
+> failure DM roughly every ~25 seconds, indefinitely (observed in the live message box).
+> This follow-up adds **throttling/de-duplication** so the failure DM is sent **once per
+> failure type until the next successful startup**, and makes the message **more
+> descriptive** (per-relay connect state + the event kinds that were needed).
+> See the "Follow-up: Throttling + Descriptive Failure DM" section at the end.
+
+# Startup Failure Admin DM Notification (original plan)
+
+## Goal
+
+When the agent fails to start, send a best-effort encrypted DM to the administrator
+describing which startup step failed and why, so the operator learns about the failure
+without having to SSH in and read `journalctl`.
+
+This directly addresses the real-world incident on VM410 where both `didactyl.service`
+and `simon.service` were stuck restart-looping at startup step 14
+(`Subscribe self-skill cache: failed (no skill events found after EOSE)`) and silently
+stopped answering DMs.
+
+## Background / Code References
+
+- Startup is a linear checklist in [`main()`](src/main.c:1012). Each step uses helpers:
+  - [`startup_step_begin()`](src/main.c:303)
+  - [`startup_step_ok()`](src/main.c:309)
+  - [`startup_step_fail()`](src/main.c:320)
+- On any fatal failure, the current pattern is:
+  `startup_step_fail(...)` -> `fprintf(stderr, ...)` -> cleanup calls -> `return 1;`
+  (e.g. the step-14 self-skill abort at [`src/main.c:1520`](src/main.c:1520)).
+- The success path already sends an admin "started up" DM at
+  [`src/main.c:1663`](src/main.c:1663) via
+  [`nostr_handler_send_dm_auto()`](src/nostr_handler.c:3264).
+- DM delivery requires (see [`nostr_handler_send_dm_with_role()`](src/nostr_handler.c:3133)):
+  - `g_cfg` and `g_pool` set (relay pool initialized),
+  - at least one **connected** relay (otherwise the kind-4 event is dropped:
+    "kind 4 event not queued: no connected relays" at [`src/nostr_handler.c:3203`](src/nostr_handler.c:3203)),
+  - a valid `cfg.admin.pubkey` (validated at step 4, [`src/main.c:1310`](src/main.c:1310)),
+  - the private key derived (always done before the checklist).
+
+### Delivery-window reality
+
+A failure DM is only *deliverable* from roughly step 11 onward (relay pool created +
+relays connected + admin known). The step-14 failure we actually hit is inside that
+window, so it will be delivered. Earlier failures (bad nsec, missing admin, LLM config,
+no relay connection) have no working channel; per decision, those are **logged only**
+(best-effort, no blocking retries).
+
+## Design Decision (confirmed)
+
+**Best-effort only.** Attempt the failure DM whenever relays + admin are available; if
+the relay pool isn't connected or admin pubkey is unknown, skip the DM and rely on
+existing stderr/journal logging. No blocking retry loop, no self-healing of the
+underlying failure (that can be a separate plan).
+
+## Approach
+
+Add a single helper that builds and sends the failure DM, then call it from every fatal
+startup-abort site (the points that currently do `startup_step_fail(...) ... return 1;`).
+
+### 1. New helper in [`src/main.c`](src/main.c)
+
+Add a static function near the other startup helpers (after
+[`startup_step_fail()`](src/main.c:320)):
+
+```c
+static void notify_admin_startup_failure(const didactyl_config_t* cfg,
+                                         int step,
+                                         const char* label,
+                                         const char* detail);
+```
+
+Behavior:
+- Guard clauses (skip + DEBUG_WARN if any precondition is missing):
+  - `cfg == NULL` or `cfg->admin.pubkey[0] == '\0'` -> log "admin unknown; cannot notify".
+  - `nostr_handler_connected_relay_count() <= 0` -> log "no connected relay; cannot notify".
+- Build a concise human-readable message, e.g.:
+  ```
+  <DisplayName> FAILED to start at <YYYY-MM-DD HH:MM:SS>.
+  Startup step [14] Subscribe self-skill cache failed: no skill events found after EOSE.
+  Version <X>. Connected relays: <n>/<m>. The agent is NOT online and will not answer DMs until fixed.
+  ```
+  - Reuse `nostr_handler_get_startup_display_name()` and `DIDACTYL_VERSION` exactly like
+    the success DM at [`src/main.c:1645`](src/main.c:1645) for naming/version consistency.
+  - Include `step`, `label`, and `detail` so each failure site is self-describing.
+- Send via `nostr_handler_send_dm_auto(cfg->admin.pubkey, msg)`; if it returns non-zero,
+  `DEBUG_WARN` that the failure DM could not be delivered (do not change the exit code).
+- Pump the poll loop briefly after sending so the async publish can flush before process
+  exit: call `nostr_handler_poll(...)` a few times (e.g. ~300--500 ms total) so the
+  queued kind-4 event is actually written to the relay sockets before cleanup/`return 1`.
+  (Without this, async publish may be discarded on immediate exit.)
+
+### 2. Wire the helper into fatal abort sites
+
+For each fatal `startup_step_fail(...)` that ends in `return 1;`, insert a call to
+`notify_admin_startup_failure(&cfg, <step>, "<label>", "<detail>")` immediately after the
+`startup_step_fail(...)` line and before the cleanup/`return 1`.
+
+Priority sites (inside the deliverable window — relay pool up + admin known):
+- Step 11 — discover self relay list failures
+  ([`src/main.c:1420`](src/main.c:1420), [`src/main.c:1437`](src/main.c:1437)).
+- Step 14 — self-skill cache failures (the incident we hit):
+  - subscribe failed ([`src/main.c:1481`](src/main.c:1481)),
+  - EOSE timeout ([`src/main.c:1496`](src/main.c:1496)),
+  - no skill events after EOSE ([`src/main.c:1521`](src/main.c:1521)).
+- Step 15 — Subscribe DMs failed ([`src/main.c:1552`](src/main.c:1552)).
+
+Earlier-window sites (relay/admin may not be ready — helper will self-skip and just log,
+but we still call it uniformly for completeness):
+- Step 1/3/4/5/6/7/8/9 fatal aborts. The helper's guard clauses make these safe no-ops
+  when delivery isn't possible.
+
+Keep the existing `fprintf(stderr, ...)` and cleanup unchanged; the DM is purely additive
+and must never alter the exit code or cleanup ordering.
+
+### 3. Message size / safety
+
+- Use a fixed stack buffer (e.g. `char msg[768];`) like the success DM at
+  [`src/main.c:1644`](src/main.c:1644).
+- `snprintf` with truncation is acceptable; `detail` strings are short and controlled.
+
+## Out of Scope
+
+- No blocking retry / wait-for-relay loop (explicitly declined).
+- No auto-remediation of the step-14 self-skill cause (e.g. auto-publishing the default
+  skill). Tracked separately if desired.
+- No change to `deploy_lt.sh` post-deploy health checks (could be a follow-up: have the
+  deploy script verify each service reaches `READY` after restart).
+
+## Verification
+
+1. Build the static binary (`build_static.sh`) and confirm no warnings.
+2. Local reproduction of step-14 failure: run an `--nsec`-only agent for an identity that
+   has connected relays but **no** published skill events, confirm:
+   - startup still aborts with exit code 1 (unchanged behavior),
+   - the admin receives a DM naming step 14 and the "no skill events found after EOSE"
+     detail.
+3. Negative case: kill relay connectivity (or use an unreachable relay) and confirm the
+   helper logs "no connected relay; cannot notify" and does not crash or hang.
+4. Confirm the success-path startup DM at [`src/main.c:1663`](src/main.c:1663) is
+   unaffected.
+5. Deploy to VM410, restart `didactyl.service` / `simon.service`, and confirm the admin
+   npub receives the failure DM while the skill events are still missing; then publish a
+   skill and confirm normal `READY` + startup DM resumes.
+
+---
+
+# Follow-up: Throttling + Descriptive Failure DM
+
+## Problems observed in production
+
+1. **DM flood.** With `Restart=on-failure` / `RestartSec=10`, the step-14 failure recurs
+   on every restart and the agent reaches the deliverable window each time, so the admin
+   gets a fresh failure DM every ~25s indefinitely (confirmed in the live message box).
+2. **Insufficient detail.** The current message names the step + detail, but not which
+   relays were attempted, whether each connected, nor which event kinds were required.
+
+## Decisions (confirmed with user)
+
+- **Throttle semantics:** send exactly once per failure type (keyed by step) until the
+  agent next starts successfully. The marker is cleared on `READY`. No periodic
+  reminders. A different failing step is a different "type" and notifies once.
+- **Descriptive content:** include the attempted relay list with per-relay connect state,
+  and the event kinds that step 14 needs (31123 / 31124 skill events; 10123 adoption list).
+
+## Part A -- Throttle / de-duplicate via on-disk marker
+
+### Marker file location (systemd-sandbox safe)
+
+- The unit runs with `WorkingDirectory=/home/<user>` and (hardened variant)
+  `ReadWritePaths=/home/<user>`, so only the agent home is writable.
+- `cfg.tools.shell.working_directory` defaults to `"."` (see
+  [`config.c`](src/config.c:1459)), which resolves to the home dir at runtime.
+- Use a hidden marker in the working directory: `./.didactyl_startup_failure`.
+  - For `didactyl` -> `/home/didactyl/.didactyl_startup_failure`
+  - For `simon` -> `/home/simon/.didactyl_startup_failure`
+  - Both inside the writable `ReadWritePaths`, so writes succeed under the sandbox.
+- Resolve the directory the same way the local-file tools do: prefer
+  `cfg->tools.shell.working_directory` when non-empty, else `"."`
+  (mirror [`tool_local.c`](src/tools/tool_local.c:49)).
+
+### Marker contents
+
+Plain text, one record, easy to parse and inspect manually:
+
+- `step=14`
+- `label=Subscribe self-skill cache`
+- `detail=no skill events found after EOSE`
+- `last_sent_epoch=1781314692`
+
+(Only `step` is strictly needed for the de-dup key; the rest aids debugging.)
+
+### New helpers in [`src/main.c`](src/main.c)
+
+Add small static helpers near
+[`notify_admin_startup_failure()`](src/main.c:331):
+
+- `startup_failure_marker_path(cfg, out, out_size)` -- builds
+  `<workdir>/.didactyl_startup_failure`.
+- `startup_failure_already_notified(cfg, step)` -- returns 1 if the marker exists AND its
+  `step=` matches the current `step` (suppress); 0 otherwise (allow). Missing/unreadable
+  marker -> 0 (allow).
+- `startup_failure_marker_write(cfg, step, label, detail)` -- writes/overwrites the marker
+  after an attempted send.
+- `startup_failure_marker_clear(cfg)` -- `remove()` the marker; ignore ENOENT.
+
+### Wiring
+
+- In [`notify_admin_startup_failure()`](src/main.c:331): after the existing guard
+  clauses (config/admin/relay), check `startup_failure_already_notified(cfg, step)`.
+  If it returns 1, log a DEBUG_INFO suppression line and return without sending.
+  - On a successful send, call `startup_failure_marker_write(cfg, step, label, detail)`.
+  - If the same step keeps failing, only the first restart in the episode sends a DM;
+    subsequent restarts find the matching marker and stay silent.
+  - If a different step fails later, the `step=` mismatch allows exactly one new DM and
+    rewrites the marker with the new step.
+- On the success path, clear the marker so the next failure episode notifies again. Add
+  `startup_failure_marker_clear(&cfg);` next to the READY success DM at
+  [`src/main.c:1663`](src/main.c:1663).
+
+### Edge cases
+
+- Marker write failure (e.g. read-only FS): log DEBUG_WARN and continue. Worst case we
+  fall back to current behavior (may re-send on next restart) -- acceptable, never fatal.
+- Two services share the binary but use different home dirs, so markers never collide.
+
+## Part B -- Descriptive failure message
+
+Enhance the message built in
+[`notify_admin_startup_failure()`](src/main.c:331) to append:
+
+1. **Attempted relays + per-relay state.** Add a compact accessor to the nostr handler:
+   - New `nostr_handler_relay_state_summary(void)` in
+     [`nostr_handler.c`](src/nostr_handler.c) / [`nostr_handler.h`](src/nostr_handler.h)
+     returning a caller-freed compact string like
+     `relay.laantungir.net=connected; relay.damus.io=connected; relay.primal.net=connecting`.
+   - Implement by reusing the existing loop over `g_cfg->relays[]` +
+     `nostr_relay_pool_get_relay_status()` + `relay_status_str()` (patterns at
+     [`src/nostr_handler.c:3183`](src/nostr_handler.c:3183) and
+     [`src/nostr_handler.c:419`](src/nostr_handler.c:419)).
+   - Preferred over embedding raw JSON from
+     [`nostr_handler_relay_status_json()`](src/nostr_handler.c:3971) to keep the DM short.
+2. **Needed event kinds (step-specific).** For step 14 append a fixed clause naming the
+   required events: kind 31123/31124 (skills) and kind 10123 (adoption list). Implement as
+   a small `startup_step_needed_events(step)` lookup in [`src/main.c`](src/main.c) that
+   returns a clause for known steps (14, 11, ...) and empty for others.
+
+### Resulting message shape (example)
+
+- `Didactyl FAILED to start at 2026-06-13 10:38:13.`
+- `Startup step [14] Subscribe self-skill cache failed: no skill events found after EOSE.`
+- `Version v0.2.48. Connected relays: 3/3.`
+- `Relays: relay.laantungir.net=connected; relay.damus.io=connected; relay.primal.net=connected.`
+- `Needed events: kind 31123/31124 (skills) and kind 10123 (adoption list) for this agent's pubkey.`
+- `The agent is NOT online and will not answer DMs until fixed.`
+
+Keep within the existing `failure_dm` buffer (bump to ~1536 if needed); `snprintf`
+truncation remains safe.
+
+## Implementation order
+
+1. Add `nostr_handler_relay_state_summary()` to handler `.c`/`.h`.
+2. Add marker helpers + `startup_step_needed_events()` to [`src/main.c`](src/main.c).
+3. Update [`notify_admin_startup_failure()`](src/main.c:331): de-dup check, richer
+   message, marker write on send.
+4. Add `startup_failure_marker_clear(&cfg)` on the READY success path
+   ([`src/main.c:1663`](src/main.c:1663)).
+5. Build (`make`), then `build_static.sh`, deploy, verify.
+
+## Verification (follow-up)
+
+1. **Throttle:** reproduce step-14 failure; confirm exactly one DM on the first failing
+   restart and no further DMs across subsequent restart-loop iterations (journal shows a
+   suppression line).
+2. **Clear-on-success:** publish a skill so startup reaches `READY`; confirm marker is
+   removed and the normal startup DM is sent.
+3. **Re-arm:** break startup again and confirm a single new DM is delivered.
+4. **Descriptive content:** confirm the DM includes the per-relay state line and the
+   needed-events clause.
+5. **Sandbox write:** on VM410 confirm the marker is created at
+   `/home/didactyl/.didactyl_startup_failure` (and `/home/simon/...`) without permission
+   errors under the systemd sandbox.

src/agent.c

@@ -35,8 +35,6 @@ static pthread_mutex_t g_context_part_names_mutex = PTHREAD_MUTEX_INITIALIZER;
 
 #define AGENT_DEBOUNCE_WINDOW_SECONDS 5
 #define AGENT_DEBOUNCE_CACHE_SIZE 256
-#define AGENT_HISTORY_TURNS 12
-#define AGENT_HISTORY_QUERY_LIMIT 200
 #define AGENT_ADOPTED_SKILLS_CACHE_TTL_SECONDS 300
 #define AGENT_ADOPTED_SKILLS_MAX 24
 #define AGENT_ADOPTED_SKILL_CONTENT_MAX_CHARS 1800
@@ -681,7 +679,21 @@ static char* build_slash_help_all_json(void) {
 
     int adopted_count = 0;
     if (adoption_events && cJSON_IsArray(adoption_events) && cJSON_GetArraySize(adoption_events) > 0) {
-        cJSON* ev0 = cJSON_GetArrayItem(adoption_events, 0);
+        cJSON* ev0 = NULL;
+        double best_created = -1.0;
+        int an = cJSON_GetArraySize(adoption_events);
+        for (int ai = 0; ai < an; ai++) {
+            cJSON* ev = cJSON_GetArrayItem(adoption_events, ai);
+            if (!ev || !cJSON_IsObject(ev)) {
+                continue;
+            }
+            cJSON* created_at = cJSON_GetObjectItemCaseSensitive(ev, "created_at");
+            double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
+            if (!ev0 || created > best_created) {
+                ev0 = ev;
+                best_created = created;
+            }
+        }
         cJSON* tags = ev0 ? cJSON_GetObjectItemCaseSensitive(ev0, "tags") : NULL;
         if (tags && cJSON_IsArray(tags)) {
             int tn = cJSON_GetArraySize(tags);
@@ -1048,73 +1060,6 @@ static __attribute__((unused)) char* build_sender_verification_text(didactyl_sen
 }
 
 
-static __attribute__((unused)) int append_recent_admin_dm_history(cJSON* messages, const char* current_message) {
-    if (!messages || !g_cfg) {
-        return -1;
-    }
-
-    char* history_json = nostr_handler_get_dm_history_json(g_cfg->admin.pubkey, AGENT_HISTORY_TURNS);
-    if (!history_json) {
-        return 0;
-    }
-
-    cJSON* items = cJSON_Parse(history_json);
-    free(history_json);
-    if (!items || !cJSON_IsArray(items)) {
-        cJSON_Delete(items);
-        return 0;
-    }
-
-    const char* last_appended_role = NULL;
-    const char* last_appended_content = NULL;
-
-    int n = cJSON_GetArraySize(items);
-    for (int i = 0; i < n; i++) {
-        cJSON* item = cJSON_GetArrayItem(items, i);
-        cJSON* role = item ? cJSON_GetObjectItemCaseSensitive(item, "role") : NULL;
-        cJSON* content = item ? cJSON_GetObjectItemCaseSensitive(item, "content") : NULL;
-        cJSON* created_at = item ? cJSON_GetObjectItemCaseSensitive(item, "created_at") : NULL;
-
-        if (!role || !content || !cJSON_IsString(role) || !cJSON_IsString(content) ||
-            !role->valuestring || !content->valuestring) {
-            continue;
-        }
-
-        const char* role_s = role->valuestring;
-        const char* content_s = content->valuestring;
-        int role_is_user = (strcmp(role_s, "user") == 0);
-        if (!role_is_user && strcmp(role_s, "assistant") != 0) {
-            continue;
-        }
-
-        if (i == n - 1 && role_is_user && current_message && strcmp(content_s, current_message) == 0) {
-            continue;
-        }
-
-        if (last_appended_role && last_appended_content &&
-            strcmp(last_appended_role, role_s) == 0 &&
-            strcmp(last_appended_content, content_s) == 0) {
-            continue;
-        }
-
-        if (append_simple_message(messages, role_s, content_s) != 0) {
-            cJSON_Delete(items);
-            return -1;
-        }
-
-        cJSON* appended = cJSON_GetArrayItem(messages, cJSON_GetArraySize(messages) - 1);
-        if (appended && cJSON_IsObject(appended) && created_at && cJSON_IsNumber(created_at)) {
-            cJSON_AddNumberToObject(appended, "_ts", created_at->valuedouble);
-        }
-
-        last_appended_role = role_s;
-        last_appended_content = content_s;
-    }
-
-    cJSON_Delete(items);
-    return 0;
-}
-
 static cJSON* find_tag_value_string_local(cJSON* tags, const char* key) {
     if (!tags || !key || !cJSON_IsArray(tags)) {
         return NULL;
@@ -1449,7 +1394,29 @@ static int refresh_adopted_skills_cache_if_needed(void) {
     free(adoption_json);
 
     if (adoption_events && cJSON_IsArray(adoption_events) && cJSON_GetArraySize(adoption_events) > 0) {
-        cJSON* list_event = cJSON_GetArrayItem(adoption_events, 0);
+        cJSON* list_event = NULL;
+        double list_event_created_at = -1.0;
+        int adoption_n = cJSON_GetArraySize(adoption_events);
+        for (int ai = 0; ai < adoption_n; ai++) {
+            cJSON* ev = cJSON_GetArrayItem(adoption_events, ai);
+            if (!ev || !cJSON_IsObject(ev)) {
+                continue;
+            }
+
+            cJSON* ev_pubkey = cJSON_GetObjectItemCaseSensitive(ev, "pubkey");
+            if (!ev_pubkey || !cJSON_IsString(ev_pubkey) || !ev_pubkey->valuestring ||
+                strcmp(ev_pubkey->valuestring, g_cfg->keys.public_key_hex) != 0) {
+                continue;
+            }
+
+            cJSON* created_at = cJSON_GetObjectItemCaseSensitive(ev, "created_at");
+            double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
+            if (!list_event || created > list_event_created_at) {
+                list_event = ev;
+                list_event_created_at = created;
+            }
+        }
+
         cJSON* list_tags = list_event ? cJSON_GetObjectItemCaseSensitive(list_event, "tags") : NULL;
 
         if (list_tags && cJSON_IsArray(list_tags)) {
@@ -1761,16 +1728,8 @@ static __attribute__((unused)) int append_adopted_skills_context(cJSON* messages
     return rc;
 }
 
-static __attribute__((unused)) cJSON* build_recent_admin_dm_history_messages(const char* current_message) {
-    cJSON* messages = cJSON_CreateArray();
-    if (!messages) {
-        return NULL;
-    }
-    if (append_recent_admin_dm_history(messages, current_message) != 0) {
-        cJSON_Delete(messages);
-        return NULL;
-    }
-    return messages;
+void agent_set_signer(nostr_signer_t* signer) {
+    tools_set_signer(&g_tools_ctx, signer);
 }
 
 int agent_init(didactyl_config_t* config) {
@@ -2182,9 +2141,11 @@ void agent_on_message(const char* sender_pubkey_hex,
 
     int max_turns = g_cfg->tools.max_turns > 0 ? g_cfg->tools.max_turns : 40;
     int stall_repeat_threshold = g_cfg->tools.stall_repeat_threshold > 1 ? g_cfg->tools.stall_repeat_threshold : 3;
+    int max_context_bytes = g_cfg->tools.max_context_bytes >= 4096 ? g_cfg->tools.max_context_bytes : (128 * 1024);
     uint64_t last_tool_fp = 0;
     int repeated_tool_turns = 0;
     int exited_on_stall = 0;
+    int exited_on_context_limit = 0;
     int stall_due_to_length = 0;
     char* final_answer_owned = NULL;
     int turns_run = 0;
@@ -2196,6 +2157,17 @@ void agent_on_message(const char* sender_pubkey_hex,
             break;
         }
 
+        size_t messages_json_len = strlen(messages_json);
+        if ((int)messages_json_len > max_context_bytes) {
+            DEBUG_WARN("[didactyl] DM tool loop context limit exceeded: bytes=%zu max_context_bytes=%d turn=%d",
+                       messages_json_len,
+                       max_context_bytes,
+                       turns_run);
+            exited_on_context_limit = 1;
+            free(messages_json);
+            break;
+        }
+
         llm_response_t resp;
         int rc = llm_chat_with_tools_messages(messages_json, tools_json, "auto", &resp);
         free(messages_json);
@@ -2275,28 +2247,35 @@ void agent_on_message(const char* sender_pubkey_hex,
         llm_response_free(&resp);
     }
 
-    if (!final_answer_owned) {
+    if (!final_answer_owned && !exited_on_context_limit) {
         char* messages_json = cJSON_PrintUnformatted(messages);
         if (messages_json) {
-            llm_response_t final_resp;
-            int final_rc = llm_chat_with_tools_messages(messages_json, tools_json, "none", &final_resp);
-            free(messages_json);
-            if (final_rc == 0) {
-                const char* forced_answer = final_resp.content ? final_resp.content : "";
-                if (forced_answer[0] != '\0') {
-                    final_answer_owned = strdup(forced_answer);
+            size_t messages_json_len = strlen(messages_json);
+            if ((int)messages_json_len <= max_context_bytes) {
+                llm_response_t final_resp;
+                int final_rc = llm_chat_with_tools_messages(messages_json, tools_json, "none", &final_resp);
+                if (final_rc == 0) {
+                    const char* forced_answer = final_resp.content ? final_resp.content : "";
+                    if (forced_answer[0] != '\0') {
+                        final_answer_owned = strdup(forced_answer);
+                    }
+                    llm_response_free(&final_resp);
                 }
-                llm_response_free(&final_resp);
+            } else {
+                exited_on_context_limit = 1;
             }
+            free(messages_json);
         }
     }
 
-    int exhausted_on_max_turns = (!final_answer_owned && !exited_on_stall && turns_run >= max_turns);
+    int exhausted_on_max_turns = (!final_answer_owned && !exited_on_stall && !exited_on_context_limit && turns_run >= max_turns);
 
     if (!final_answer_owned) {
-        final_answer_owned = strdup(exited_on_stall
-                                        ? "I stopped repeated tool calls after detecting a loop and could not produce a final summary."
-                                        : "I reached the tool-turn limit before getting a final response from the model.");
+        final_answer_owned = strdup(exited_on_context_limit
+                                        ? "I paused because the working context became too large while using tools. Please narrow the scope and ask me to continue from a smaller context."
+                                        : (exited_on_stall
+                                               ? "I stopped repeated tool calls after detecting a loop and could not produce a final summary."
+                                               : "I reached the tool-turn limit before getting a final response from the model."));
     }
 
     if (exhausted_on_max_turns) {
@@ -2313,17 +2292,25 @@ void agent_on_message(const char* sender_pubkey_hex,
 
     const char* final_answer = final_answer_owned ? final_answer_owned : "I reached the tool-turn limit before getting a final response from the model.";
 
-    if (exited_on_stall || exhausted_on_max_turns) {
+    if (exited_on_stall || exhausted_on_max_turns || exited_on_context_limit) {
         notify_admin_limit_diagnostic("dm_agent_loop",
-                                      exited_on_stall ? "stall_repetition_detected" : "max_turns_exhausted",
+                                      exited_on_context_limit
+                                          ? "max_context_bytes_exceeded"
+                                          : (exited_on_stall ? "stall_repetition_detected" : "max_turns_exhausted"),
                                       sender_pubkey_hex,
                                       max_turns,
                                       turns_run,
                                       stall_repeat_threshold,
                                       repeated_tool_turns,
                                       g_cfg->llm.max_tokens,
-                                      (exited_on_stall && stall_due_to_length) ? "max_tokens_truncation" : NULL,
-                                      (exited_on_stall && stall_due_to_length) ? "Increase max_tokens (example: /model_set {\"max_tokens\": 4096})" : NULL,
+                                      exited_on_context_limit
+                                          ? "tool_context_growth"
+                                          : ((exited_on_stall && stall_due_to_length) ? "max_tokens_truncation" : NULL),
+                                      exited_on_context_limit
+                                          ? "Reduce tool-loop breadth or lower max_turns; context exceeded max_context_bytes."
+                                          : ((exited_on_stall && stall_due_to_length)
+                                                 ? "Increase max_tokens (example: /model_set {\"max_tokens\": 4096})"
+                                                 : NULL),
                                       final_answer);
     }
     fprintf(stdout, "[didactyl] final response: %.240s%s\n",

src/agent.h

@@ -9,6 +9,10 @@
 struct trigger_manager;
 
 int agent_init(didactyl_config_t* config);
+/* Wire a process-lifetime signer handle (non-owning) into the agent's tools
+ * context so NIP-04/44 encrypt/decrypt tool call sites route through the
+ * signer. Must be called after agent_init. Caller retains ownership. */
+void agent_set_signer(nostr_signer_t* signer);
 void agent_set_trigger_manager(struct trigger_manager* trigger_manager);
 void agent_on_trigger(const char* skill_d_tag,
                       const char* skill_content,

src/cashu_wallet.c

@@ -19,6 +19,13 @@
 #define CASHU_WALLET_QUERY_TIMEOUT_MS 6000
 #define CASHU_WALLET_MAX_SPLIT_PARTS 64
 
+/* Optional process-lifetime signer for NIP-60/NIP-61 cashu event creation.
+ * Owned by main.c; non-owning here. When present, event creation is routed
+ * through the *_with_signer variants so the raw private key stays out of the
+ * agent process in remote-signer modes. When NULL, the legacy raw-key path is
+ * used (local-mode compatibility fallback). */
+static nostr_signer_t* g_cashu_signer = NULL;
+
 typedef struct {
     char event_id[65];
     nostr_nip60_token_data_t token;
@@ -121,7 +128,12 @@ static int publish_from_signed_event_template(cJSON* ev_template, char out_event
 }
 
 static int publish_wallet_event_and_store_locked(const nostr_nip60_wallet_data_t* wallet_data, char out_event_id[65]) {
-    cJSON* ev = nostr_nip60_create_wallet_event(wallet_data, g_wallet.cfg->keys.private_key, time(NULL));
+    cJSON* ev = NULL;
+    if (g_cashu_signer) {
+        ev = nostr_nip60_create_wallet_event_with_signer(wallet_data, g_cashu_signer, time(NULL));
+    } else {
+        ev = nostr_nip60_create_wallet_event(wallet_data, g_wallet.cfg->keys.private_key, time(NULL));
+    }
     if (!ev) return -1;
 
     int rc = publish_from_signed_event_template(ev, out_event_id);
@@ -156,7 +168,12 @@ static int publish_wallet_event_and_store_locked(const nostr_nip60_wallet_data_t
 static int publish_token_event_and_store_locked(nostr_nip60_token_data_t* token_data, char out_event_id[65]) {
     if (!token_data) return -1;
 
-    cJSON* ev = nostr_nip60_create_token_event(token_data, g_wallet.cfg->keys.private_key, time(NULL));
+    cJSON* ev = NULL;
+    if (g_cashu_signer) {
+        ev = nostr_nip60_create_token_event_with_signer(token_data, g_cashu_signer, time(NULL));
+    } else {
+        ev = nostr_nip60_create_token_event(token_data, g_wallet.cfg->keys.private_key, time(NULL));
+    }
     if (!ev) return -1;
 
     char event_id[65] = {0};
@@ -194,7 +211,12 @@ static int publish_history_event(nostr_nip60_direction_t direction,
     history.refs = &ref;
     history.ref_count = (ref.event_id[0] != '\0') ? 1 : 0;
 
-    cJSON* ev = nostr_nip60_create_history_event(&history, g_wallet.cfg->keys.private_key, time(NULL));
+    cJSON* ev = NULL;
+    if (g_cashu_signer) {
+        ev = nostr_nip60_create_history_event_with_signer(&history, g_cashu_signer, time(NULL));
+    } else {
+        ev = nostr_nip60_create_history_event(&history, g_wallet.cfg->keys.private_key, time(NULL));
+    }
     if (!ev) return -1;
 
     int rc = publish_from_signed_event_template(ev, NULL);
@@ -203,7 +225,12 @@ static int publish_history_event(nostr_nip60_direction_t direction,
 }
 
 static int publish_token_deletion_event(const char* event_id) {
-    cJSON* del = nostr_nip60_create_token_deletion(event_id, g_wallet.cfg->keys.private_key, time(NULL));
+    cJSON* del = NULL;
+    if (g_cashu_signer) {
+        del = nostr_nip60_create_token_deletion_with_signer(event_id, g_cashu_signer, time(NULL));
+    } else {
+        del = nostr_nip60_create_token_deletion(event_id, g_wallet.cfg->keys.private_key, time(NULL));
+    }
     if (!del) return -1;
     int rc = publish_from_signed_event_template(del, NULL);
     cJSON_Delete(del);
@@ -408,6 +435,15 @@ int cashu_wallet_init(didactyl_config_t* cfg) {
     return 0;
 }
 
+void cashu_wallet_set_signer(nostr_signer_t* signer) {
+    /* Non-owning: the signer handle is constructed and freed by main.c.
+     * Stored under the wallet mutex for visibility/tearing safety even
+     * though the handle itself is process-lifetime and immutable. */
+    pthread_mutex_lock(&g_wallet.mutex);
+    g_cashu_signer = signer;
+    pthread_mutex_unlock(&g_wallet.mutex);
+}
+
 void cashu_wallet_cleanup(void) {
     if (!g_wallet.initialized) return;
 
@@ -2755,7 +2791,12 @@ int cashu_wallet_mints_set(const char** wallet_mints,
         pthread_mutex_unlock(&g_wallet.mutex);
         if (rc != 0) return -1;
 
-        cJSON* ev = nostr_nip61_create_nutzap_info_event(&info, g_wallet.cfg->keys.private_key, time(NULL));
+        cJSON* ev = NULL;
+        if (g_cashu_signer) {
+            ev = nostr_nip61_create_nutzap_info_event_with_signer(&info, g_cashu_signer, time(NULL));
+        } else {
+            ev = nostr_nip61_create_nutzap_info_event(&info, g_wallet.cfg->keys.private_key, time(NULL));
+        }
         nostr_nip61_free_nutzap_info(&info);
         if (!ev) return -1;
 

src/cashu_wallet.h

@@ -5,8 +5,10 @@
 
 #include "config.h"
 #include "cjson/cJSON.h"
+#include "../nostr_core_lib/nostr_core/nostr_signer.h"
 
 int cashu_wallet_init(didactyl_config_t* cfg);
+void cashu_wallet_set_signer(nostr_signer_t* signer);
 void cashu_wallet_cleanup(void);
 
 int cashu_wallet_load_from_relays(void);

src/config.c

@@ -214,6 +214,97 @@ static int decode_pubkey_hex_or_npub(const char* in, char out_hex[65]) {
     return -1;
 }
 
+/* Returns 1 if mode is a known signer mode, 0 otherwise. */
+static int signer_mode_is_known(const char* mode) {
+    if (!mode || mode[0] == '\0') {
+        return 0;
+    }
+    return strcmp(mode, "local") == 0 ||
+           strcmp(mode, "nsigner_unix") == 0 ||
+           strcmp(mode, "nsigner_tcp") == 0;
+}
+
+/* Returns 1 if mode is a remote (nsigner_*) mode that does not require an
+ * in-process nsec, 0 otherwise. */
+static int signer_mode_is_remote(const char* mode) {
+    if (!mode || mode[0] == '\0') {
+        return 0;
+    }
+    return strcmp(mode, "nsigner_unix") == 0 ||
+           strcmp(mode, "nsigner_tcp") == 0;
+}
+
+static int parse_signer_config(cJSON* root, didactyl_config_t* config) {
+    cJSON* signer = cJSON_GetObjectItemCaseSensitive(root, "signer");
+    if (!signer || !cJSON_IsObject(signer)) {
+        /* Missing signer block: defaults already applied by caller. */
+        return 0;
+    }
+
+    if (copy_json_string(signer, "mode", config->signer.mode,
+                         sizeof(config->signer.mode), 0) != 0) {
+        config_set_error("signer.mode must be a string when provided");
+        return -1;
+    }
+    if (config->signer.mode[0] != '\0' && !signer_mode_is_known(config->signer.mode)) {
+        config_set_error("signer.mode '%s' is not a known signer mode "
+                         "(expected: local, nsigner_unix, nsigner_tcp)",
+                         config->signer.mode);
+        return -1;
+    }
+
+    if (copy_json_string(signer, "socket_name", config->signer.socket_name,
+                         sizeof(config->signer.socket_name), 0) != 0) {
+        config_set_error("signer.socket_name must be a string when provided");
+        return -1;
+    }
+
+    if (copy_json_string(signer, "role", config->signer.role,
+                         sizeof(config->signer.role), 0) != 0) {
+        config_set_error("signer.role must be a string when provided");
+        return -1;
+    }
+
+    cJSON* timeout = cJSON_GetObjectItemCaseSensitive(signer, "timeout_ms");
+    if (timeout && cJSON_IsNumber(timeout)) {
+        int t = (int)timeout->valuedouble;
+        if (t > 0) {
+            config->signer.timeout_ms = t;
+        }
+    }
+
+    if (copy_json_string(signer, "auth_privkey_hex", config->signer.auth_privkey_hex,
+                         sizeof(config->signer.auth_privkey_hex), 0) != 0) {
+        config_set_error("signer.auth_privkey_hex must be a string when provided");
+        return -1;
+    }
+
+    /* Optional tcp host/port inside the signer block (alternative to --signer-tcp). */
+    if (copy_json_string(signer, "tcp_host", config->signer.tcp_host,
+                         sizeof(config->signer.tcp_host), 0) != 0) {
+        config_set_error("signer.tcp_host must be a string when provided");
+        return -1;
+    }
+    cJSON* tcp_port = cJSON_GetObjectItemCaseSensitive(signer, "tcp_port");
+    if (tcp_port && cJSON_IsNumber(tcp_port)) {
+        int p = (int)tcp_port->valuedouble;
+        if (p > 0 && p <= 65535) {
+            config->signer.tcp_port = p;
+        }
+    }
+
+    /* Phase 4 item 20: optional emergency local nsec for admin-alert fallback.
+     * Parsed and stored only; no active fallback behavior is wired yet. */
+    if (copy_json_string(signer, "emergency_local_nsec",
+                         config->signer.emergency_local_nsec,
+                         sizeof(config->signer.emergency_local_nsec), 0) != 0) {
+        config_set_error("signer.emergency_local_nsec must be a string when provided");
+        return -1;
+    }
+
+    return 0;
+}
+
 static int parse_tools_config(cJSON* root, didactyl_config_t* config) {
     cJSON* tools = cJSON_GetObjectItemCaseSensitive(root, "tools");
     if (!tools || !cJSON_IsObject(tools)) {
@@ -226,6 +317,7 @@ static int parse_tools_config(cJSON* root, didactyl_config_t* config) {
     cJSON* api_default_max_turns = cJSON_GetObjectItemCaseSensitive(tools, "api_default_max_turns");
     cJSON* api_max_turns_ceiling = cJSON_GetObjectItemCaseSensitive(tools, "api_max_turns_ceiling");
     cJSON* stall_repeat_threshold = cJSON_GetObjectItemCaseSensitive(tools, "stall_repeat_threshold");
+    cJSON* max_context_bytes = cJSON_GetObjectItemCaseSensitive(tools, "max_context_bytes");
     cJSON* local_http_fetch_default_timeout_seconds =
         cJSON_GetObjectItemCaseSensitive(tools, "local_http_fetch_default_timeout_seconds");
     cJSON* local_http_fetch_max_timeout_seconds =
@@ -252,6 +344,9 @@ static int parse_tools_config(cJSON* root, didactyl_config_t* config) {
     if (stall_repeat_threshold && cJSON_IsNumber(stall_repeat_threshold)) {
         config->tools.stall_repeat_threshold = (int)stall_repeat_threshold->valuedouble;
     }
+    if (max_context_bytes && cJSON_IsNumber(max_context_bytes)) {
+        config->tools.max_context_bytes = (int)max_context_bytes->valuedouble;
+    }
     if (local_http_fetch_default_timeout_seconds && cJSON_IsNumber(local_http_fetch_default_timeout_seconds)) {
         config->tools.local_http_fetch_default_timeout_seconds =
             (int)local_http_fetch_default_timeout_seconds->valuedouble;
@@ -311,6 +406,9 @@ static int parse_tools_config(cJSON* root, didactyl_config_t* config) {
     if (config->tools.stall_repeat_threshold < 2) {
         config->tools.stall_repeat_threshold = 3;
     }
+    if (config->tools.max_context_bytes < 4096) {
+        config->tools.max_context_bytes = 128 * 1024;
+    }
     if (config->tools.local_http_fetch_default_timeout_seconds < 1) {
         config->tools.local_http_fetch_default_timeout_seconds = 20;
     }
@@ -1441,6 +1539,7 @@ int config_load(const char* path, didactyl_config_t* config) {
     config->tools.api_default_max_turns = 8;
     config->tools.api_max_turns_ceiling = 32;
     config->tools.stall_repeat_threshold = 3;
+    config->tools.max_context_bytes = 128 * 1024;
     config->tools.local_http_fetch_default_timeout_seconds = 20;
     config->tools.local_http_fetch_max_timeout_seconds = 120;
     config->tools.blossom_max_upload_bytes = 16 * 1024 * 1024;
@@ -1483,6 +1582,18 @@ int config_load(const char* path, didactyl_config_t* config) {
     config->cashu_wallet.auto_load = 1;
     config->cashu_wallet.mint_timeout_seconds = 30;
 
+    /* Signer provider defaults: local mode, backward compatible. */
+    snprintf(config->signer.mode, sizeof(config->signer.mode), "%s", "local");
+    config->signer.socket_name[0] = '\0';
+    snprintf(config->signer.role, sizeof(config->signer.role), "%s", "main");
+    config->signer.timeout_ms = 15000;
+    config->signer.auth_privkey_hex[0] = '\0';
+    config->signer.tcp_host[0] = '\0';
+    config->signer.tcp_port = 0;
+    /* Phase 4 item 20: emergency local nsec placeholder. Off by default;
+     * no active fallback behavior yet (documentation/feature-flag only). */
+    config->signer.emergency_local_nsec[0] = '\0';
+
     char* raw_buf = NULL;
     size_t raw_len = 0;
     if (read_file_to_buffer(path, &raw_buf, &raw_len) != 0) {
@@ -1617,7 +1728,15 @@ int config_load(const char* path, didactyl_config_t* config) {
         goto cleanup;
     }
 
-    if (config->keys.nsec[0] != '\0') {
+    if (parse_signer_config(root, config) != 0) {
+        /* parse_signer_config sets a specific error message. */
+        goto cleanup;
+    }
+
+    /* Only decode the raw private key in local mode. In remote (nsigner_*)
+     * modes the agent process never holds the nsec; the pubkey is learned
+     * from the signer at startup via nostr_signer_get_public_key(). */
+    if (!signer_mode_is_remote(config->signer.mode) && config->keys.nsec[0] != '\0') {
         if (decode_private_key(config->keys.nsec, config->keys.private_key) != 0) {
             config_set_error("keys.nsec/key.nsec must be valid nsec1... or 64-char hex private key");
             goto cleanup;

src/config.h

@@ -8,6 +8,11 @@
 #define OW_MAX_URL_LEN 256
 #define OW_MAX_KEY_LEN 256
 #define OW_MAX_MODEL_LEN 128
+#define OW_MAX_SIGNER_MODE_LEN 32
+#define OW_MAX_SIGNER_SOCKET_LEN 128
+#define OW_MAX_SIGNER_ROLE_LEN 32
+#define OW_MAX_SIGNER_HOST_LEN 128
+#define OW_MAX_SIGNER_AUTH_HEX_LEN 65
 
 #define OW_MAX_STRANGER_RESPONSE_LEN 512
 
@@ -51,6 +56,7 @@ typedef struct {
     int api_default_max_turns;
     int api_max_turns_ceiling;
     int stall_repeat_threshold;
+    int max_context_bytes;
     int local_http_fetch_default_timeout_seconds;
     int local_http_fetch_max_timeout_seconds;
     shell_tools_config_t shell;
@@ -115,6 +121,45 @@ typedef struct {
     int mint_timeout_seconds;
 } cashu_wallet_config_t;
 
+/* Signer provider configuration.
+ *
+ * mode selects how signing/encryption operations are routed:
+ *   "local"        - raw 32-byte key held in cfg.keys.private_key (default,
+ *                    backward compatible, output-equivalent to legacy path).
+ *   "nsigner_unix" - delegate to a running n_signer over an AF_UNIX abstract
+ *                    socket. The agent process holds no nsec.
+ *   "nsigner_tcp"  - delegate to a running n_signer over TCP (host:port).
+ *                    Requires auth_privkey_hex for the kind-27235 auth envelope.
+ *
+ * Missing signer block behaves as mode="local" using keys.nsec.
+ * In any nsigner_* mode, keys.nsec is optional and ignored; the agent pubkey
+ * is learned from the signer via nostr_signer_get_public_key().
+ */
+typedef struct {
+    char mode[OW_MAX_SIGNER_MODE_LEN];          /* "local" | "nsigner_unix" | "nsigner_tcp" */
+    char socket_name[OW_MAX_SIGNER_SOCKET_LEN]; /* nsigner_unix: abstract socket name (without @); "" = auto-discover */
+    char role[OW_MAX_SIGNER_ROLE_LEN];          /* n_signer role selector (default "main") */
+    int timeout_ms;                             /* per-call timeout (default 15000) */
+    char auth_privkey_hex[OW_MAX_SIGNER_AUTH_HEX_LEN]; /* optional, TCP auth envelope only */
+    /* nsigner_tcp parsed host/port (populated from --signer-tcp or config) */
+    char tcp_host[OW_MAX_SIGNER_HOST_LEN];
+    int tcp_port;
+    /* Optional emergency local nsec for admin-alert fallback (Phase 4 item 20).
+     *
+     * OFF by default (empty string). When populated AND a remote signer is
+     * unreachable, a future phase may use this in-process key ONLY to sign a
+     * minimal admin alert DM reporting the signer outage. This reintroduces
+     * the nsec into the agent process for that one purpose, which is a
+     * deliberate operator-accepted tradeoff: better to leak the nsec briefly
+     * to notify the admin than to fail silently.
+     *
+     * CURRENT STATUS: parsed and stored only. No active fallback behavior is
+     * implemented yet (feature flag / documentation placeholder). The field
+     * exists so operators can pre-stage the value; the fallback path is
+     * deferred until the supervisor/health surface (item 19) is proven. */
+    char emergency_local_nsec[OW_MAX_KEY_LEN];  /* "" = disabled (default) */
+} signer_config_t;
+
 typedef struct {
     agent_keys_t keys;
     admin_config_t admin;
@@ -128,6 +173,7 @@ typedef struct {
     triggers_config_t triggers;
     api_config_t api;
     cashu_wallet_config_t cashu_wallet;
+    signer_config_t signer;
     startup_event_t* startup_events;
     int startup_event_count;
     encrypted_event_t* encrypted_events;

src/http_api.c

@@ -17,6 +17,7 @@
 #include "cjson/cJSON.h"
 #include "debug.h"
 #include "mongoose.h"
+#include "signer_health.h"
 
 static http_api_context_t g_api_ctx;
 static int g_api_initialized = 0;
@@ -815,7 +816,21 @@ static char* build_slash_help_all_json_local(void) {
 
     int adopted_count = 0;
     if (adoption_events && cJSON_IsArray(adoption_events) && cJSON_GetArraySize(adoption_events) > 0) {
-        cJSON* ev0 = cJSON_GetArrayItem(adoption_events, 0);
+        cJSON* ev0 = NULL;
+        double best_created = -1.0;
+        int an = cJSON_GetArraySize(adoption_events);
+        for (int ai = 0; ai < an; ai++) {
+            cJSON* ev = cJSON_GetArrayItem(adoption_events, ai);
+            if (!ev || !cJSON_IsObject(ev)) {
+                continue;
+            }
+            cJSON* created_at = cJSON_GetObjectItemCaseSensitive(ev, "created_at");
+            double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
+            if (!ev0 || created > best_created) {
+                ev0 = ev;
+                best_created = created;
+            }
+        }
         cJSON* tags = ev0 ? cJSON_GetObjectItemCaseSensitive(ev0, "tags") : NULL;
         if (tags && cJSON_IsArray(tags)) {
             int tn = cJSON_GetArraySize(tags);
@@ -1214,6 +1229,39 @@ static void handle_status(struct mg_connection* c) {
     if (g_api_ctx.cfg) {
         cJSON_AddStringToObject(root, "pubkey", g_api_ctx.cfg->keys.public_key_hex);
         cJSON_AddNumberToObject(root, "relay_count", g_api_ctx.cfg->relay_count);
+        /* Phase 4 item 19: out-of-band signer health surface. Expose the
+         * configured signer mode and runtime health classification so an
+         * operator can detect a signing outage from the HTTP status endpoint
+         * without requiring a signed admin DM to come back. */
+        cJSON_AddStringToObject(root, "signer_mode",
+                                g_api_ctx.cfg->signer.mode[0] ? g_api_ctx.cfg->signer.mode : "local");
+    }
+
+    /* Signer runtime health (process-global, lock-protected snapshot). */
+    signer_health_snapshot_t hs;
+    if (signer_health_snapshot(&hs) == 0) {
+        const char* state_str = "unknown";
+        if (hs.state == SIGNER_HEALTH_HEALTHY) {
+            state_str = "healthy";
+        } else if (hs.state == SIGNER_HEALTH_UNHEALTHY) {
+            state_str = "unhealthy";
+        }
+        cJSON_AddStringToObject(root, "signer_healthy",
+                                hs.state == SIGNER_HEALTH_HEALTHY ? "true" :
+                                hs.state == SIGNER_HEALTH_UNHEALTHY ? "false" : "unknown");
+        cJSON_AddStringToObject(root, "signer_health_state", state_str);
+        cJSON_AddStringToObject(root, "signer_last_error",
+                                hs.last_reason[0] ? hs.last_reason : "");
+        if (hs.last_error_ts > 0) {
+            cJSON_AddNumberToObject(root, "signer_last_error_ts", (double)hs.last_error_ts);
+        } else {
+            cJSON_AddNullToObject(root, "signer_last_error_ts");
+        }
+        if (hs.last_ok_ts > 0) {
+            cJSON_AddNumberToObject(root, "signer_last_ok_ts", (double)hs.last_ok_ts);
+        } else {
+            cJSON_AddNullToObject(root, "signer_last_ok_ts");
+        }
     }
 
     cJSON_AddNumberToObject(root, "connected_relays", nostr_handler_connected_relay_count());

src/main.h

@@ -12,8 +12,8 @@
 // Using DIDACTYL_ prefix to avoid conflicts with nostr_core_lib VERSION macros
 #define DIDACTYL_VERSION_MAJOR 0
 #define DIDACTYL_VERSION_MINOR 2
-#define DIDACTYL_VERSION_PATCH 35
-#define DIDACTYL_VERSION "v0.2.35"
+#define DIDACTYL_VERSION_PATCH 53
+#define DIDACTYL_VERSION "v0.2.53"
 
 // Agent metadata
 #define DIDACTYL_NAME "Didactyl"

src/nostr_block_list.c

@@ -10,6 +10,10 @@
 #include "debug.h"
 #include "../../nostr_core_lib/nostr_core/nostr_core.h"
 
+/* Optional process-lifetime signer for NIP-44 encrypt/decrypt of private
+ * block-list content. Owned by main.c; non-owning here. */
+static nostr_signer_t* g_block_signer = NULL;
+
 typedef struct {
     didactyl_config_t* cfg;
     int initialized;
@@ -186,22 +190,43 @@ static int decrypt_private_tags_array(const char* encrypted_content, cJSON** out
         return *out_array ? 0 : -1;
     }
 
-    size_t cap = strlen(encrypted_content) + 4096;
-    char* plaintext = (char*)calloc(1, cap);
-    if (!plaintext) return -1;
+    /* Phase 3 item 13: route NIP-44 decrypt through the process signer when
+     * available so remote signer modes keep the nsec out of the agent. The
+     * signer verb returns a heap string via out-param; free it after parse.
+     * Falls back to the legacy raw-key path when no signer is set. */
+    const char* plain_src = NULL;
+    char* plain_to_free = NULL;
+    char* plaintext = NULL;
 
-    int rc = nostr_nip44_decrypt(g_block.cfg->keys.private_key,
-                                 g_block.cfg->keys.public_key,
-                                 encrypted_content,
-                                 plaintext,
-                                 cap);
-    if (rc != 0) {
-        free(plaintext);
-        return -1;
+    if (g_block_signer) {
+        int rc = nostr_signer_nip44_decrypt(g_block_signer,
+                                            g_block.cfg->keys.public_key_hex,
+                                            encrypted_content,
+                                            &plaintext);
+        if (rc != NOSTR_SUCCESS || !plaintext) {
+            return -1;
+        }
+        plain_src = plaintext;
+        plain_to_free = plaintext;
+    } else {
+        size_t cap = strlen(encrypted_content) + 4096;
+        plaintext = (char*)calloc(1, cap);
+        if (!plaintext) return -1;
+        int rc = nostr_nip44_decrypt(g_block.cfg->keys.private_key,
+                                     g_block.cfg->keys.public_key,
+                                     encrypted_content,
+                                     plaintext,
+                                     cap);
+        if (rc != 0) {
+            free(plaintext);
+            return -1;
+        }
+        plain_src = plaintext;
+        plain_to_free = plaintext;
     }
 
-    cJSON* arr = cJSON_Parse(plaintext);
-    free(plaintext);
+    cJSON* arr = cJSON_Parse(plain_src);
+    free(plain_to_free);
     if (!arr || !cJSON_IsArray(arr)) {
         cJSON_Delete(arr);
         return -1;
@@ -218,8 +243,25 @@ static int encrypt_private_tags_array(cJSON* private_tags_array, char** out_cont
     char* plain = cJSON_PrintUnformatted(private_tags_array);
     if (!plain) return -1;
 
+    /* Phase 3 item 13: route NIP-44 encrypt through the process signer when
+     * available. The signer verb returns a heap string via out-param. Falls
+     * back to the legacy raw-key path when no signer is set. */
+    char* cipher = NULL;
+    if (g_block_signer) {
+        int rc = nostr_signer_nip44_encrypt(g_block_signer,
+                                            g_block.cfg->keys.public_key_hex,
+                                            plain,
+                                            &cipher);
+        free(plain);
+        if (rc != NOSTR_SUCCESS || !cipher) {
+            return -1;
+        }
+        *out_content = cipher;
+        return 0;
+    }
+
     size_t cap = strlen(plain) * 4 + 4096;
-    char* cipher = (char*)calloc(1, cap);
+    cipher = (char*)calloc(1, cap);
     if (!cipher) {
         free(plain);
         return -1;
@@ -311,6 +353,12 @@ static int publish_kind10000(cJSON* public_tags, cJSON* private_tags, char* out_
     return 0;
 }
 
+void nostr_block_list_set_signer(nostr_signer_t* signer) {
+    pthread_mutex_lock(&g_block.mutex);
+    g_block_signer = signer;
+    pthread_mutex_unlock(&g_block.mutex);
+}
+
 int nostr_block_list_init(didactyl_config_t* cfg) {
     if (!cfg) return -1;
 
@@ -365,6 +413,7 @@ void nostr_block_list_cleanup(void) {
     g_block.cfg = NULL;
     g_block.loaded = 0;
     g_block.initialized = 0;
+    g_block_signer = NULL;
     pthread_mutex_unlock(&g_block.mutex);
 }
 

src/nostr_block_list.h

@@ -3,11 +3,19 @@
 
 #include "config.h"
 #include "cjson/cJSON.h"
+#include "../nostr_core_lib/nostr_core/nostr_signer.h"
 
 int nostr_block_list_init(didactyl_config_t* cfg);
 int nostr_block_list_load_from_relays(void);
 void nostr_block_list_cleanup(void);
 
+/* Wire a process-lifetime signer handle (non-owning) so NIP-44 encrypt/decrypt
+ * of the private block-list content routes through the signer verbs in remote
+ * signer modes. Falls back to the legacy raw-key path when NULL. The caller
+ * must keep the signer alive for the module's lifetime and free it after
+ * nostr_block_list_cleanup. */
+void nostr_block_list_set_signer(nostr_signer_t* signer);
+
 int nostr_block_list_is_pubkey_blocked(const char* pubkey_hex);
 int nostr_block_list_is_event_blocked(const char* event_id_hex);
 int nostr_block_list_is_hashtag_blocked(const char* hashtag);

src/nostr_handler.c

@@ -15,6 +15,7 @@
 #include "nostr_block_list.h"
 #include "cashu_wallet.h"
 #include "agent.h"
+#include "signer_health.h"
 
 /*
  * Older nostr_core_lib versions only expose:
@@ -34,6 +35,8 @@
 
 static didactyl_config_t* g_cfg = NULL;
 static nostr_relay_pool_t* g_pool = NULL;
+/* Optional process-lifetime signer for relay pool AUTH. Owned by main.c. */
+static nostr_signer_t* g_auth_signer = NULL;
 static dm_callback_t g_dm_callback = NULL;
 static void* g_dm_user_data = NULL;
 static int g_poll_counter = 0;
@@ -1048,6 +1051,26 @@ static int nip44_encrypt_self_local(const char* plaintext, char** out_ciphertext
     }
 
     const char* plain = plaintext ? plaintext : "";
+
+    /* Phase 3 item 13: route self-encrypt through the process signer when
+     * available so remote signer modes keep the nsec out of the agent. The
+     * signer verb returns a heap string via out-param. Falls back to the
+     * legacy raw-key path when no signer is set (local mode / pre-Phase-3). */
+    if (g_auth_signer) {
+        char* signer_out = NULL;
+        int rc = nostr_signer_nip44_encrypt(g_auth_signer,
+                                            g_cfg->keys.public_key_hex,
+                                            plain,
+                                            &signer_out);
+        if (rc != NOSTR_SUCCESS || !signer_out) {
+            signer_health_record_failure(rc, "nip44_encrypt(self)");
+            return -1;
+        }
+        signer_health_record_ok();
+        *out_ciphertext = signer_out;
+        return 0;
+    }
+
     size_t out_cap = (strlen(plain) * 4U) + 1024U;
     char* ciphertext = (char*)malloc(out_cap);
     if (!ciphertext) {
@@ -1073,6 +1096,23 @@ static int nip44_decrypt_self_local(const char* ciphertext, char** out_plaintext
         return -1;
     }
 
+    /* Phase 3 item 13: route self-decrypt through the process signer when
+     * available. Falls back to the legacy raw-key path when no signer is set. */
+    if (g_auth_signer) {
+        char* signer_out = NULL;
+        int rc = nostr_signer_nip44_decrypt(g_auth_signer,
+                                            g_cfg->keys.public_key_hex,
+                                            ciphertext,
+                                            &signer_out);
+        if (rc != NOSTR_SUCCESS || !signer_out) {
+            signer_health_record_failure(rc, "nip44_decrypt(self)");
+            return -1;
+        }
+        signer_health_record_ok();
+        *out_plaintext = signer_out;
+        return 0;
+    }
+
     size_t out_cap = strlen(ciphertext) + 1024U;
     char* plaintext = (char*)malloc(out_cap);
     if (!plaintext) {
@@ -1510,6 +1550,7 @@ static void register_trigger_from_self_skill_event(cJSON* event) {
 
 static void self_skill_cache_upsert_event_locked(cJSON* event) {
     if (!event || !cJSON_IsObject(event)) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: event missing or not object");
         return;
     }
 
@@ -1517,34 +1558,51 @@ static void self_skill_cache_upsert_event_locked(cJSON* event) {
     cJSON* pubkey = cJSON_GetObjectItemCaseSensitive(event, "pubkey");
     cJSON* tags = cJSON_GetObjectItemCaseSensitive(event, "tags");
     cJSON* created_at = cJSON_GetObjectItemCaseSensitive(event, "created_at");
+    cJSON* ev_id = cJSON_GetObjectItemCaseSensitive(event, "id");
+
+    int kind_val = (kind && cJSON_IsNumber(kind)) ? (int)kind->valuedouble : -1;
+    double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
+
+    DEBUG_INFO("[didactyl] self-skill upsert candidate: kind=%d author=%.16s... id=%.16s... created_at=%.0f",
+               kind_val,
+               (pubkey && cJSON_IsString(pubkey) && pubkey->valuestring) ? pubkey->valuestring : "?",
+               (ev_id && cJSON_IsString(ev_id) && ev_id->valuestring) ? ev_id->valuestring : "?",
+               created);
 
     if (!kind || !cJSON_IsNumber(kind) ||
         !pubkey || !cJSON_IsString(pubkey) || !pubkey->valuestring ||
         !tags || !cJSON_IsArray(tags)) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: missing required kind/pubkey/tags");
         return;
     }
 
-    int kind_val = (int)kind->valuedouble;
     if (kind_val != 31123 && kind_val != 31124 && kind_val != 10123) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: kind not in {31123,31124,10123}");
         return;
     }
 
     if (!g_cfg) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: config unavailable");
         return;
     }
 
     int is_agent_author = (strcmp(pubkey->valuestring, g_cfg->keys.public_key_hex) == 0);
     int is_admin_author = (g_cfg->admin.pubkey[0] != '\0' && strcmp(pubkey->valuestring, g_cfg->admin.pubkey) == 0);
-    if (!is_agent_author && !is_admin_author) {
-        return;
+    if (kind_val == 10123) {
+        if (!is_agent_author) {
+            DEBUG_INFO("[didactyl] self-skill upsert rejected: kind=10123 author is not self");
+            return;
+        }
     }
 
-    if (is_admin_author && kind_val != 31123) {
+    if (is_admin_author && kind_val == 31124) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: admin cannot own private skill (31124)");
         return;
     }
 
     const char* d_tag = find_tag_value_local(tags, "d");
     if ((kind_val == 31123 || kind_val == 31124) && (!d_tag || d_tag[0] == '\0')) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: parameterized kind missing d-tag");
         return;
     }
 
@@ -1552,12 +1610,11 @@ static void self_skill_cache_upsert_event_locked(cJSON* event) {
         cJSON_Delete(g_self_skill_events);
         g_self_skill_events = cJSON_CreateArray();
         if (!g_self_skill_events) {
+            DEBUG_INFO("[didactyl] self-skill upsert rejected: failed to create cache array");
             return;
         }
     }
 
-    double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
-
     int n = cJSON_GetArraySize(g_self_skill_events);
     for (int i = 0; i < n; i++) {
         cJSON* existing = cJSON_GetArrayItem(g_self_skill_events, i);
@@ -1589,23 +1646,56 @@ static void self_skill_cache_upsert_event_locked(cJSON* event) {
         cJSON* ex_created_at = cJSON_GetObjectItemCaseSensitive(existing, "created_at");
         double ex_created = (ex_created_at && cJSON_IsNumber(ex_created_at)) ? ex_created_at->valuedouble : 0.0;
         if (created < ex_created) {
+            DEBUG_INFO("[didactyl] self-skill upsert rejected: stale (existing created_at=%.0f >= new created_at=%.0f)",
+                       ex_created,
+                       created);
             return;
         }
 
         cJSON* dup = cJSON_Duplicate(event, 1);
         if (!dup) {
+            DEBUG_INFO("[didactyl] self-skill upsert rejected: failed to duplicate event");
             return;
         }
 
         cJSON_ReplaceItemInArray(g_self_skill_events, i, dup);
+        DEBUG_INFO("[didactyl] self-skill upsert accepted: replaced existing (old created_at=%.0f)", ex_created);
+        if (kind_val == 10123) {
+            int a_count = 0;
+            cJSON* t;
+            cJSON_ArrayForEach(t, tags) {
+                if (cJSON_IsArray(t) && cJSON_GetArraySize(t) >= 2) {
+                    cJSON* t0 = cJSON_GetArrayItem(t, 0);
+                    if (t0 && cJSON_IsString(t0) && t0->valuestring && strcmp(t0->valuestring, "a") == 0) {
+                        a_count++;
+                    }
+                }
+            }
+            DEBUG_INFO("[didactyl] kind 10123 accepted with %d 'a' tags", a_count);
+        }
         return;
     }
 
     cJSON* dup = cJSON_Duplicate(event, 1);
     if (!dup) {
+        DEBUG_INFO("[didactyl] self-skill upsert rejected: failed to duplicate event");
         return;
     }
     cJSON_AddItemToArray(g_self_skill_events, dup);
+    DEBUG_INFO("[didactyl] self-skill upsert accepted: new entry added");
+    if (kind_val == 10123) {
+        int a_count = 0;
+        cJSON* t;
+        cJSON_ArrayForEach(t, tags) {
+            if (cJSON_IsArray(t) && cJSON_GetArraySize(t) >= 2) {
+                cJSON* t0 = cJSON_GetArrayItem(t, 0);
+                if (t0 && cJSON_IsString(t0) && t0->valuestring && strcmp(t0->valuestring, "a") == 0) {
+                    a_count++;
+                }
+            }
+        }
+        DEBUG_INFO("[didactyl] kind 10123 accepted with %d 'a' tags", a_count);
+    }
 }
 
 static int hex_to_pubkey(const char* hex, unsigned char out_pubkey[32]) {
@@ -1868,19 +1958,38 @@ static void on_event(cJSON* event, const char* relay_url, void* user_data) {
             return;
         }
 
-        decrypted = (char*)malloc(NOSTR_NIP04_MAX_PLAINTEXT_SIZE);
-        if (!decrypted) {
-            fprintf(stderr, "[didactyl] failed to allocate DM decrypt buffer\n");
-            return;
-        }
-        decrypted[0] = '\0';
-
         trace_event_json("received encrypted DM event:", event);
 
-        if (nostr_nip04_decrypt(g_cfg->keys.private_key, sender_pubkey, content->valuestring, decrypted, NOSTR_NIP04_MAX_PLAINTEXT_SIZE) != NOSTR_SUCCESS) {
-            fprintf(stdout, "[didactyl] failed to decrypt incoming DM from %.16s...\n", sender_pubkey_hex);
-            free(decrypted);
-            return;
+        /* Phase 3 item 13: route NIP-04 decrypt through the process signer
+         * when available so remote signer modes keep the nsec out of the
+         * agent. The signer verb returns a heap string via out-param. Falls
+         * back to the legacy raw-key path when no signer is set. */
+        if (g_auth_signer) {
+            char* signer_out = NULL;
+            int dec_rc = nostr_signer_nip04_decrypt(g_auth_signer,
+                                           sender_pubkey_hex,
+                                           content->valuestring,
+                                           &signer_out);
+            if (dec_rc != NOSTR_SUCCESS || !signer_out) {
+                signer_health_record_failure(dec_rc, "nip04_decrypt(incoming DM)");
+                fprintf(stdout, "[didactyl] failed to decrypt incoming DM from %.16s...\n", sender_pubkey_hex);
+                return;
+            }
+            signer_health_record_ok();
+            decrypted = signer_out;
+        } else {
+            decrypted = (char*)malloc(NOSTR_NIP04_MAX_PLAINTEXT_SIZE);
+            if (!decrypted) {
+                fprintf(stderr, "[didactyl] failed to allocate DM decrypt buffer\n");
+                return;
+            }
+            decrypted[0] = '\0';
+
+            if (nostr_nip04_decrypt(g_cfg->keys.private_key, sender_pubkey, content->valuestring, decrypted, NOSTR_NIP04_MAX_PLAINTEXT_SIZE) != NOSTR_SUCCESS) {
+                fprintf(stdout, "[didactyl] failed to decrypt incoming DM from %.16s...\n", sender_pubkey_hex);
+                free(decrypted);
+                return;
+            }
         }
 
         trace_plaintext_dm("received decrypted DM content:", decrypted);
@@ -1891,7 +2000,16 @@ static void on_event(cJSON* event, const char* relay_url, void* user_data) {
             return;
         }
 
-        cJSON* rumor = nostr_nip17_receive_dm(event, g_cfg->keys.private_key);
+        /* Phase 3 item 14: prefer signer-aware NIP-17 unwrap when a process
+         * signer is available; fall back to the legacy raw-key path in local
+         * mode / pre-Phase-3. Gift-wrap event ownership is unchanged: the
+         * returned rumor cJSON is owned by us and freed below. */
+        cJSON* rumor = NULL;
+        if (g_auth_signer) {
+            rumor = nostr_nip17_receive_dm_with_signer(event, g_auth_signer);
+        } else {
+            rumor = nostr_nip17_receive_dm(event, g_cfg->keys.private_key);
+        }
         if (!rumor) {
             DEBUG_TRACE("[didactyl] DEBUG on_event: failed to unwrap/decrypt NIP-17 gift wrap %.16s...",
                         event_id_hex ? event_id_hex : "<no-id>");
@@ -2470,6 +2588,10 @@ static void on_wallet_event(cJSON* event, const char* relay_url, void* user_data
     (void)cashu_wallet_load_from_relays();
 }
 
+void nostr_handler_set_signer(nostr_signer_t* signer) {
+    g_auth_signer = signer;
+}
+
 int nostr_handler_init(didactyl_config_t* config) {
     if (!config) {
         return -1;
@@ -2512,16 +2634,28 @@ int nostr_handler_init(didactyl_config_t* config) {
     nostr_pool_reconnect_config_t reconnect = *nostr_pool_reconnect_config_default();
     reconnect.enable_auto_reconnect = 1;
     reconnect.ping_interval_seconds = 20;
-    reconnect.pong_timeout_seconds = 10;
+    reconnect.pong_timeout_seconds = 30;
 
     g_pool = nostr_relay_pool_create(&reconnect);
     if (!g_pool) {
         return -1;
     }
 
-    if (nostr_relay_pool_set_auth(g_pool, g_cfg->keys.private_key, 1) != NOSTR_SUCCESS) {
-        fprintf(stderr, "[didactyl] failed to enable relay pool auth\n");
-        return -1;
+    /* Relay pool NIP-42 AUTH. When a process-lifetime signer is available
+     * (set via nostr_handler_set_signer), route AUTH signing through it so
+     * remote signer modes can keep the nsec out of the agent process. In
+     * local mode the signer wraps the same raw key, so behavior is identical.
+     * Falls back to the legacy raw-key path when no signer is set. */
+    if (g_auth_signer) {
+        if (nostr_relay_pool_set_auth_with_signer(g_pool, g_auth_signer, 1) != NOSTR_SUCCESS) {
+            fprintf(stderr, "[didactyl] failed to enable relay pool auth (signer path)\n");
+            return -1;
+        }
+    } else {
+        if (nostr_relay_pool_set_auth(g_pool, g_cfg->keys.private_key, 1) != NOSTR_SUCCESS) {
+            fprintf(stderr, "[didactyl] failed to enable relay pool auth\n");
+            return -1;
+        }
     }
 
     for (int i = 0; i < g_cfg->relay_count; i++) {
@@ -2773,6 +2907,10 @@ int nostr_handler_subscribe_self_skills(void) {
     cJSON_AddItemToObject(filter, "authors", authors);
     cJSON_AddNumberToObject(filter, "limit", 300);
 
+    char* filter_str = cJSON_PrintUnformatted(filter);
+    DEBUG_INFO("[didactyl] self-skill subscription filter: %s", filter_str ? filter_str : "(null)");
+    free(filter_str);
+
     pthread_mutex_lock(&g_subscription_mutex);
     managed_subscriptions_init_defaults();
     if (managed_subscription_register_locked(MANAGED_SUB_SELF_SKILLS,
@@ -3090,16 +3228,33 @@ int nostr_handler_send_dm_with_role(const char* recipient_pubkey_hex,
 
     trace_plaintext_dm("sending plaintext DM content:", message);
 
-    char* encrypted = (char*)malloc(NOSTR_NIP04_MAX_ENCRYPTED_SIZE);
-    if (!encrypted) {
-        fprintf(stderr, "[didactyl] failed to allocate DM encrypt buffer\n");
-        return -1;
-    }
-    encrypted[0] = '\0';
+    /* Phase 3 item 13: route NIP-04 encrypt through the process signer when
+     * available so remote signer modes keep the nsec out of the agent. The
+     * signer verb returns a heap string via out-param. Falls back to the
+     * legacy raw-key path when no signer is set. */
+    char* encrypted = NULL;
+    if (g_auth_signer) {
+        int enc_rc = nostr_signer_nip04_encrypt(g_auth_signer,
+                                       recipient_pubkey_hex,
+                                       message,
+                                       &encrypted);
+        if (enc_rc != NOSTR_SUCCESS || !encrypted) {
+            signer_health_record_failure(enc_rc, "nip04_encrypt(outgoing DM)");
+            return -1;
+        }
+        signer_health_record_ok();
+    } else {
+        encrypted = (char*)malloc(NOSTR_NIP04_MAX_ENCRYPTED_SIZE);
+        if (!encrypted) {
+            fprintf(stderr, "[didactyl] failed to allocate DM encrypt buffer\n");
+            return -1;
+        }
+        encrypted[0] = '\0';
 
-    if (nostr_nip04_encrypt(g_cfg->keys.private_key, recipient_pubkey, message, encrypted, NOSTR_NIP04_MAX_ENCRYPTED_SIZE) != NOSTR_SUCCESS) {
-        free(encrypted);
-        return -1;
+        if (nostr_nip04_encrypt(g_cfg->keys.private_key, recipient_pubkey, message, encrypted, NOSTR_NIP04_MAX_ENCRYPTED_SIZE) != NOSTR_SUCCESS) {
+            free(encrypted);
+            return -1;
+        }
     }
 
     cJSON* tags = create_dm_tags_for_recipient(recipient_pubkey_hex);
@@ -3108,7 +3263,17 @@ int nostr_handler_send_dm_with_role(const char* recipient_pubkey_hex,
         return -1;
     }
 
-    cJSON* event = nostr_create_and_sign_event(4, encrypted, tags, g_cfg->keys.private_key, time(NULL));
+    /* Phase 3 item 12: route kind-4 DM event signing through the process
+     * signer handle when available so remote signer modes can keep the nsec
+     * out of the agent process. Falls back to the legacy raw-key path when
+     * no signer is set (local mode / pre-Phase-2 binaries) so behavior is
+     * unchanged. */
+    cJSON* event = NULL;
+    if (g_auth_signer) {
+        event = nostr_create_and_sign_event_with_signer(4, encrypted, tags, g_auth_signer, time(NULL));
+    } else {
+        event = nostr_create_and_sign_event(4, encrypted, tags, g_cfg->keys.private_key, time(NULL));
+    }
     cJSON_Delete(tags);
     free(encrypted);
     if (!event) {
@@ -3247,7 +3412,17 @@ static int publish_kind_event_to_relays(int kind,
         }
     }
 
-    cJSON* event = nostr_create_and_sign_event(kind, content_to_publish, tags_copy, g_cfg->keys.private_key, time(NULL));
+    /* Phase 3 item 12: route generic kind event signing through the process
+     * signer handle when available (covers kind 30078 config publish, kind
+     * 31124 private skill events, startup adoption events, etc.). Falls back
+     * to the legacy raw-key path when no signer is set so local mode is
+     * unchanged. */
+    cJSON* event = NULL;
+    if (g_auth_signer) {
+        event = nostr_create_and_sign_event_with_signer(kind, content_to_publish, tags_copy, g_auth_signer, time(NULL));
+    } else {
+        event = nostr_create_and_sign_event(kind, content_to_publish, tags_copy, g_cfg->keys.private_key, time(NULL));
+    }
     if (tags_copy) {
         cJSON_Delete(tags_copy);
     }
@@ -3694,6 +3869,180 @@ char* nostr_handler_get_self_skill_events_json(void) {
     return json ? json : strdup("[]");
 }
 
+int nostr_handler_refresh_self_skill_cache_from_relays(int timeout_ms) {
+    if (!g_cfg || !g_pool) {
+        return -1;
+    }
+
+    int effective_timeout_ms = timeout_ms > 0 ? timeout_ms : 5000;
+
+    cJSON* filter = cJSON_CreateObject();
+    cJSON* kinds = cJSON_CreateArray();
+    cJSON* authors = cJSON_CreateArray();
+    if (!filter || !kinds || !authors) {
+        cJSON_Delete(filter);
+        cJSON_Delete(kinds);
+        cJSON_Delete(authors);
+        return -1;
+    }
+
+    cJSON_AddItemToArray(kinds, cJSON_CreateNumber(31123));
+    cJSON_AddItemToArray(kinds, cJSON_CreateNumber(31124));
+    cJSON_AddItemToArray(kinds, cJSON_CreateNumber(10123));
+    cJSON_AddItemToObject(filter, "kinds", kinds);
+
+    cJSON_AddItemToArray(authors, cJSON_CreateString(g_cfg->keys.public_key_hex));
+    cJSON_AddItemToObject(filter, "authors", authors);
+    cJSON_AddNumberToObject(filter, "limit", 500);
+
+    char* events_json = nostr_handler_query_json(filter, effective_timeout_ms);
+    cJSON_Delete(filter);
+    if (!events_json) {
+        return -1;
+    }
+
+    cJSON* events = cJSON_Parse(events_json);
+    free(events_json);
+    if (!events || !cJSON_IsArray(events)) {
+        cJSON_Delete(events);
+        return -1;
+    }
+
+    cJSON* adopted_authors = cJSON_CreateObject();
+    if (adopted_authors) {
+        cJSON* latest_self_adoption = NULL;
+        double latest_self_adoption_created = -1.0;
+        int n0 = cJSON_GetArraySize(events);
+        for (int i = 0; i < n0; i++) {
+            cJSON* ev = cJSON_GetArrayItem(events, i);
+            if (!ev || !cJSON_IsObject(ev)) {
+                continue;
+            }
+
+            cJSON* kind = cJSON_GetObjectItemCaseSensitive(ev, "kind");
+            cJSON* pubkey = cJSON_GetObjectItemCaseSensitive(ev, "pubkey");
+            if (!kind || !cJSON_IsNumber(kind) || (int)kind->valuedouble != 10123 ||
+                !pubkey || !cJSON_IsString(pubkey) || !pubkey->valuestring ||
+                strcmp(pubkey->valuestring, g_cfg->keys.public_key_hex) != 0) {
+                continue;
+            }
+
+            cJSON* created_at = cJSON_GetObjectItemCaseSensitive(ev, "created_at");
+            double created = (created_at && cJSON_IsNumber(created_at)) ? created_at->valuedouble : 0.0;
+            if (!latest_self_adoption || created > latest_self_adoption_created) {
+                latest_self_adoption = ev;
+                latest_self_adoption_created = created;
+            }
+        }
+
+        if (latest_self_adoption) {
+            cJSON* tags = cJSON_GetObjectItemCaseSensitive(latest_self_adoption, "tags");
+            if (tags && cJSON_IsArray(tags)) {
+                int tn = cJSON_GetArraySize(tags);
+                for (int ti = 0; ti < tn; ti++) {
+                    cJSON* tag = cJSON_GetArrayItem(tags, ti);
+                    if (!tag || !cJSON_IsArray(tag) || cJSON_GetArraySize(tag) < 2) {
+                        continue;
+                    }
+                    cJSON* k = cJSON_GetArrayItem(tag, 0);
+                    cJSON* v = cJSON_GetArrayItem(tag, 1);
+                    if (!k || !v || !cJSON_IsString(k) || !k->valuestring ||
+                        !cJSON_IsString(v) || !v->valuestring || strcmp(k->valuestring, "a") != 0) {
+                        continue;
+                    }
+
+                    int adopted_kind = 0;
+                    char adopted_pubkey[65] = {0};
+                    char adopted_d_tag[65] = {0};
+                    if (parse_skill_address_local(v->valuestring, &adopted_kind, adopted_pubkey, adopted_d_tag) != 0) {
+                        continue;
+                    }
+                    if (adopted_pubkey[0] == '\0') {
+                        continue;
+                    }
+                    if (!cJSON_GetObjectItemCaseSensitive(adopted_authors, adopted_pubkey)) {
+                        cJSON_AddBoolToObject(adopted_authors, adopted_pubkey, 1);
+                    }
+                }
+            }
+        }
+
+        int adopted_author_count = 0;
+        cJSON* adopted_it = NULL;
+        cJSON_ArrayForEach(adopted_it, adopted_authors) {
+            adopted_author_count++;
+        }
+
+        if (adopted_author_count > 0) {
+            cJSON* adopted_filter = cJSON_CreateObject();
+            cJSON* adopted_kinds = cJSON_CreateArray();
+            cJSON* adopted_author_arr = cJSON_CreateArray();
+            if (adopted_filter && adopted_kinds && adopted_author_arr) {
+                cJSON_AddItemToArray(adopted_kinds, cJSON_CreateNumber(31123));
+                cJSON_AddItemToArray(adopted_kinds, cJSON_CreateNumber(31124));
+                cJSON_AddItemToObject(adopted_filter, "kinds", adopted_kinds);
+
+                cJSON_ArrayForEach(adopted_it, adopted_authors) {
+                    if (adopted_it->string && adopted_it->string[0] != '\0') {
+                        cJSON_AddItemToArray(adopted_author_arr, cJSON_CreateString(adopted_it->string));
+                    }
+                }
+                cJSON_AddItemToObject(adopted_filter, "authors", adopted_author_arr);
+                cJSON_AddNumberToObject(adopted_filter, "limit", 1000);
+
+                char* adopted_json = nostr_handler_query_json(adopted_filter, effective_timeout_ms);
+                if (adopted_json) {
+                    cJSON* adopted_events = cJSON_Parse(adopted_json);
+                    free(adopted_json);
+                    if (adopted_events && cJSON_IsArray(adopted_events)) {
+                        int an = cJSON_GetArraySize(adopted_events);
+                        for (int ai = 0; ai < an; ai++) {
+                            cJSON* ev = cJSON_GetArrayItem(adopted_events, ai);
+                            cJSON* dup = ev ? cJSON_Duplicate(ev, 1) : NULL;
+                            if (dup) {
+                                cJSON_AddItemToArray(events, dup);
+                            }
+                        }
+                    }
+                    cJSON_Delete(adopted_events);
+                }
+            } else {
+                cJSON_Delete(adopted_filter);
+                cJSON_Delete(adopted_kinds);
+                cJSON_Delete(adopted_author_arr);
+            }
+            cJSON_Delete(adopted_filter);
+        }
+    }
+    cJSON_Delete(adopted_authors);
+
+    int merged = 0;
+    pthread_mutex_lock(&g_self_skill_mutex);
+    int n = cJSON_GetArraySize(events);
+    for (int i = 0; i < n; i++) {
+        cJSON* ev = cJSON_GetArrayItem(events, i);
+        if (!ev || !cJSON_IsObject(ev)) {
+            continue;
+        }
+
+        cJSON* kind = cJSON_GetObjectItemCaseSensitive(ev, "kind");
+        int kind_val = (kind && cJSON_IsNumber(kind)) ? (int)kind->valuedouble : -1;
+        if (kind_val == 31124) {
+            (void)normalize_private_skill_event_local(ev);
+        }
+
+        self_skill_cache_upsert_event_locked(ev);
+        merged++;
+    }
+    pthread_mutex_unlock(&g_self_skill_mutex);
+
+    cJSON_Delete(events);
+
+    agent_invalidate_adopted_skills_cache();
+    DEBUG_INFO("[didactyl] skill_refresh relay reload merged %d self-skill/adoption events", merged);
+    return 0;
+}
+
 int nostr_handler_is_event_in_self_cache(const char* event_id_hex) {
     if (!event_id_hex || strlen(event_id_hex) != 64U) {
         return 0;
@@ -3740,6 +4089,50 @@ int nostr_handler_connected_relay_count(void) {
     return connected;
 }
 
+char* nostr_handler_relay_state_summary(void) {
+    if (!g_cfg || !g_pool || g_cfg->relay_count <= 0 || !g_cfg->relays) {
+        return NULL;
+    }
+
+    size_t total = 1;
+    for (int i = 0; i < g_cfg->relay_count; i++) {
+        const char* relay = (g_cfg->relays[i] && g_cfg->relays[i][0] != '\0') ? g_cfg->relays[i] : "<unknown>";
+        const char* status = relay_status_str(nostr_relay_pool_get_relay_status(g_pool, relay));
+        total += strlen(relay) + 1 + strlen(status) + 2;
+    }
+
+    char* out = (char*)malloc(total);
+    if (!out) {
+        return NULL;
+    }
+
+    out[0] = '\0';
+    size_t used = 0;
+    for (int i = 0; i < g_cfg->relay_count; i++) {
+        const char* relay = (g_cfg->relays[i] && g_cfg->relays[i][0] != '\0') ? g_cfg->relays[i] : "<unknown>";
+        const char* status = relay_status_str(nostr_relay_pool_get_relay_status(g_pool, relay));
+        int n = snprintf(out + used,
+                         total - used,
+                         "%s%s=%s",
+                         (i == 0) ? "" : "; ",
+                         relay,
+                         status);
+        if (n < 0) {
+            free(out);
+            return NULL;
+        }
+
+        size_t written = (size_t)n;
+        if (written >= (total - used)) {
+            used = total - 1;
+            break;
+        }
+        used += written;
+    }
+
+    return out;
+}
+
 char* nostr_handler_relay_status_json(void) {
     if (!g_pool) {
         return NULL;
@@ -4087,14 +4480,29 @@ int nostr_handler_send_dm_nip17_with_role(const char* recipient_pubkey_hex,
         return -1;
     }
 
+    /* Phase 3 item 14: prefer signer-aware NIP-17 gift-wrap creation when a
+     * process signer is available; fall back to the legacy raw-key path in
+     * local mode / pre-Phase-3. Gift-wrap ownership is unchanged: each
+     * non-NULL entry in gift_wraps[] is freed by cJSON_Delete below. */
     cJSON* gift_wraps[NIP17_MAX_GIFT_WRAPS] = {0};
-    int gift_count = nostr_nip17_send_dm(chat_event,
+    int gift_count = 0;
+    if (g_auth_signer) {
+        gift_count = nostr_nip17_send_dm_with_signer(chat_event,
+                                                     recipients,
+                                                     1,
+                                                     g_auth_signer,
+                                                     gift_wraps,
+                                                     NIP17_MAX_GIFT_WRAPS,
+                                                     0);
+    } else {
+        gift_count = nostr_nip17_send_dm(chat_event,
                                          recipients,
                                          1,
                                          g_cfg->keys.private_key,
                                          gift_wraps,
                                          NIP17_MAX_GIFT_WRAPS,
                                          0);
+    }
     cJSON_Delete(chat_event);
     if (gift_count <= 0) {
         DEBUG_WARN("[didactyl] NIP-17 send aborted: gift_wrap creation failed for %.16s...",
@@ -4658,6 +5066,7 @@ void nostr_handler_cleanup(void) {
 
     g_pool = NULL;
     g_cfg = NULL;
+    g_auth_signer = NULL;
     g_dm_callback = NULL;
     g_dm_user_data = NULL;
     memset(g_seen_dm_ids, 0, sizeof(g_seen_dm_ids));

src/nostr_handler.h

@@ -40,6 +40,15 @@ typedef struct {
 typedef void (*nostr_self_skill_eose_cb_t)(int event_count, void* user_data);
 
 int nostr_handler_init(didactyl_config_t* config);
+
+/* Optional: provide a process-lifetime signer handle for relay pool AUTH.
+ * When set, nostr_handler_init routes NIP-42 AUTH through the signer via
+ * nostr_relay_pool_set_auth_with_signer instead of the raw private-key path.
+ * The caller retains ownership of the signer and must free it after
+ * nostr_handler_cleanup. If not called, the legacy raw-key AUTH path is used
+ * (backward compatible). */
+void nostr_handler_set_signer(nostr_signer_t* signer);
+
 void nostr_handler_set_trigger_manager(struct trigger_manager* trigger_manager);
 int nostr_handler_subscribe_admin_context(void);
 int nostr_handler_subscribe_agent_context(void);
@@ -77,9 +86,11 @@ int nostr_handler_validate_self_skill_cache(int* out_skill_count, int* out_adopt
 void nostr_handler_refresh_relay_statuses(void);
 int nostr_handler_sync_relays_from_config(void);
 char* nostr_handler_get_self_skill_events_json(void);
+int nostr_handler_refresh_self_skill_cache_from_relays(int timeout_ms);
 int nostr_handler_is_event_in_self_cache(const char* event_id_hex);
 const char* nostr_handler_get_startup_display_name(void);
 int nostr_handler_connected_relay_count(void);
+char* nostr_handler_relay_state_summary(void);
 char* nostr_handler_get_admin_kind0_context(void);
 char* nostr_handler_get_admin_kind3_context(void);
 char* nostr_handler_get_admin_kind10002_context(void);

src/setup_wizard.c

@@ -276,6 +276,7 @@ static void config_set_defaults(didactyl_config_t* cfg) {
     cfg->tools.api_default_max_turns = 8;
     cfg->tools.api_max_turns_ceiling = 32;
     cfg->tools.stall_repeat_threshold = 3;
+    cfg->tools.max_context_bytes = 128 * 1024;
     cfg->tools.local_http_fetch_default_timeout_seconds = 20;
     cfg->tools.local_http_fetch_max_timeout_seconds = 120;
     cfg->tools.blossom_max_upload_bytes = 16 * 1024 * 1024;
@@ -315,6 +316,13 @@ static void config_set_defaults(didactyl_config_t* cfg) {
     snprintf(cfg->llm.base_url, sizeof(cfg->llm.base_url), "%s", "https://api.openai.com/v1");
     cfg->llm.max_tokens = 512;
     cfg->llm.temperature = 0.7;
+
+    /* Signer provider defaults: local mode, backward compatible.
+     * Without these, apply_signer_overrides() in main.c rejects an empty
+     * signer.mode after the wizard returns BOOTSTRAP for local paths. */
+    snprintf(cfg->signer.mode, sizeof(cfg->signer.mode), "%s", "local");
+    snprintf(cfg->signer.role, sizeof(cfg->signer.role), "%s", "main");
+    cfg->signer.timeout_ms = 15000;
 }
 
 static void free_relays_only(didactyl_config_t* cfg) {
@@ -993,6 +1001,15 @@ static int fetch_and_decrypt_self_config_wizard(const didactyl_config_t* cfg, co
         return -1;
     }
 
+    /* Phase 3 item 13: DEFERRED — the setup wizard runs before any
+     * process-lifetime signer is constructed. In local mode (the only mode
+     * the wizard persists keys for) the nsec is held directly by the wizard,
+     * so the raw-key path is correct and output-equivalent. The nsigner_unix
+     * wizard path only does an ephemeral connectivity check and frees its
+     * signer immediately; it does not recall/persist encrypted user-settings.
+     * Migrating this site would require threading an ephemeral signer through
+     * the wizard for no separation benefit, so it is intentionally left on
+     * the legacy raw-key path. */
     int dec_rc = nostr_nip44_decrypt(cfg->keys.private_key,
                                      cfg->keys.public_key,
                                      content->valuestring,
@@ -1140,6 +1157,10 @@ static int publish_encrypted_self_config_wizard(const didactyl_config_t* cfg,
     char* ciphertext = (char*)malloc(cipher_cap);
     if (!ciphertext) return -1;
 
+    /* Phase 3 item 13: DEFERRED — see the matching note in the wizard's
+     * fetch_self_config_plaintext. The wizard holds the nsec directly in
+     * local mode and has no process-lifetime signer, so the raw-key path is
+     * correct here. */
     int enc_rc = nostr_nip44_encrypt(cfg->keys.private_key,
                                      cfg->keys.public_key,
                                      content_json,
@@ -1207,6 +1228,15 @@ static int persist_runtime_config_to_nostr_wizard(const didactyl_config_t* cfg)
     cJSON_AddNumberToObject(didactyl, "max_turns", cfg->tools.max_turns > 0 ? cfg->tools.max_turns : 40);
     cJSON_AddItemToObject(user_settings, "didactyl", didactyl);
 
+    cJSON* signer = cJSON_CreateObject();
+    if (signer) {
+        cJSON_AddStringToObject(signer, "mode", cfg->signer.mode);
+        cJSON_AddStringToObject(signer, "socket_name", cfg->signer.socket_name);
+        cJSON_AddStringToObject(signer, "role", cfg->signer.role);
+        cJSON_AddNumberToObject(signer, "timeout_ms", cfg->signer.timeout_ms);
+        cJSON_AddItemToObject(user_settings, "signer", signer);
+    }
+
     char* settings_json = cJSON_PrintUnformatted(user_settings);
     cJSON_Delete(user_settings);
     if (!settings_json) return -1;
@@ -1908,7 +1938,10 @@ static int write_sudoers_file(const char* service_user) {
 }
 
 static int install_system_service_with_dedicated_user(const didactyl_config_t* cfg, const char* agent_name) {
-    if (!cfg || cfg->keys.nsec[0] == '\0') return -1;
+    /* local mode requires an nsec to embed in ExecStart; remote signer modes
+       do not hold the nsec and instead pass --signer flags. */
+    if (!cfg) return -1;
+    if (strcmp(cfg->signer.mode, "local") == 0 && cfg->keys.nsec[0] == '\0') return -1;
 
     if (geteuid() != 0) {
         fprintf(stderr, "  Requesting sudo authentication for system install...\n");
@@ -2006,6 +2039,33 @@ static int install_system_service_with_dedicated_user(const didactyl_config_t* c
         snprintf(env_line, sizeof(env_line), "Environment=SSL_CERT_FILE=%s\\n", ca_bundle);
     }
 
+    /* Build the key/signer argument tail for ExecStart.
+     * - local mode: embeds the nsec directly (legacy behavior).
+     * - nsigner_unix mode: passes --signer/--signer-socket/--signer-role/--signer-timeout
+     *   so the service process reconstructs the remote signer without holding the nsec.
+     * - nsigner_tcp mode: passes --signer-tcp host:port plus role/timeout.
+     * The agent pubkey, admin, LLM and relays are recovered from Nostr at boot. */
+    char key_args[768] = {0};
+    if (strcmp(cfg->signer.mode, "nsigner_unix") == 0) {
+        snprintf(key_args, sizeof(key_args),
+                 "--signer nsigner_unix --signer-role %s --signer-timeout %d%s%s",
+                 cfg->signer.role[0] ? cfg->signer.role : "main",
+                 cfg->signer.timeout_ms > 0 ? cfg->signer.timeout_ms : 15000,
+                 cfg->signer.socket_name[0] ? " --signer-socket " : "",
+                 cfg->signer.socket_name[0] ? cfg->signer.socket_name : "");
+    } else if (strcmp(cfg->signer.mode, "nsigner_tcp") == 0) {
+        char host_port[OW_MAX_SIGNER_HOST_LEN + 16] = {0};
+        snprintf(host_port, sizeof(host_port), "%s:%d", cfg->signer.tcp_host, cfg->signer.tcp_port);
+        snprintf(key_args, sizeof(key_args),
+                 "--signer-tcp %s --signer-role %s --signer-timeout %d",
+                 host_port,
+                 cfg->signer.role[0] ? cfg->signer.role : "main",
+                 cfg->signer.timeout_ms > 0 ? cfg->signer.timeout_ms : 15000);
+    } else {
+        /* local mode (default): embed the nsec directly in ExecStart. */
+        snprintf(key_args, sizeof(key_args), "--nsec %s", cfg->keys.nsec);
+    }
+
     char service_content[8192] = {0};
     int svc_len = snprintf(service_content,
                            sizeof(service_content),
@@ -2014,11 +2074,13 @@ static int install_system_service_with_dedicated_user(const didactyl_config_t* c
                            "After=network-online.target\n"
                            "Wants=network-online.target\n\n"
                            "[Service]\n"
-                           "Type=simple\n"
+                           "Type=notify\n"
+                           "NotifyAccess=main\n"
+                           "WatchdogSec=120\n"
                            "User=%s\n"
                            "Group=%s\n"
                            "WorkingDirectory=%s\n"
-                           "ExecStart=%s --nsec %s --debug 3\n"
+                           "ExecStart=%s --debug 3 %s\n"
                            "%s"
                            "SyslogIdentifier=%s\n"
                            "NoNewPrivileges=false\n"
@@ -2037,7 +2099,7 @@ static int install_system_service_with_dedicated_user(const didactyl_config_t* c
                            service_user,
                            home,
                            bin_path,
-                           cfg->keys.nsec,
+                           key_args,
                            env_line,
                            service_user,
                            home);
@@ -2073,7 +2135,11 @@ static int install_system_service_with_dedicated_user(const didactyl_config_t* c
     fprintf(stderr, "  User:     %s\n", service_user);
     fprintf(stderr, "  Home:     %s\n", home);
     fprintf(stderr, "  Binary:   %s\n", bin_path);
-    fprintf(stderr, "  Nsec:     embedded directly in ExecStart\n");
+    if (strcmp(cfg->signer.mode, "local") == 0) {
+        fprintf(stderr, "  Nsec:     embedded directly in ExecStart\n");
+    } else {
+        fprintf(stderr, "  Signer:   %s (nsec held by n_signer, not the agent)\n", cfg->signer.mode);
+    }
     fprintf(stderr, "  Sudoers:  /etc/sudoers.d/%s\n", service_user);
     fprintf(stderr, "  Unit:     %s\n", service_path);
     fprintf(stderr, "\n  Useful commands:\n");
@@ -2115,10 +2181,11 @@ static int new_agent_identity_step(didactyl_config_t* cfg) {
         render_wizard_page_header("Step 2 of 7", "New Agent Setup -- Identity");
         print_option('g', "enerate a new Nostr keypair");
         print_option('p', "rovide an existing nsec");
+        print_option('s', "ign with a running n_signer");
         print_option('b', "ack");
         print_option('q', "uit");
-        wizard_option_t opts[] = {{'g', ""}, {'p', ""}, {'b', ""}, {'q', ""}};
-        char c = read_menu_choice(opts, 4);
+        wizard_option_t opts[] = {{'g', ""}, {'p', ""}, {'s', ""}, {'b', ""}, {'q', ""}};
+        char c = read_menu_choice(opts, 5);
         if (c == 'q') return -1;
         if (c == 'b') return 1;
 
@@ -2168,6 +2235,38 @@ static int new_agent_identity_step(didactyl_config_t* cfg) {
             }
         }
 
+        if (c == 's') {
+            snprintf(cfg->signer.mode, sizeof(cfg->signer.mode), "%s", "nsigner_unix");
+            if (read_line_prompt("  Socket name (empty for auto-discovery): ", cfg->signer.socket_name, sizeof(cfg->signer.socket_name)) != 0) return -1;
+            if (read_line_prompt("  Role [main]: ", cfg->signer.role, sizeof(cfg->signer.role)) != 0) return -1;
+            if (cfg->signer.role[0] == '\0') snprintf(cfg->signer.role, sizeof(cfg->signer.role), "%s", "main");
+            char timeout_buf[32] = {0};
+            if (read_line_prompt("  Timeout ms [15000]: ", timeout_buf, sizeof(timeout_buf)) != 0) return -1;
+            cfg->signer.timeout_ms = (timeout_buf[0] != '\0') ? atoi(timeout_buf) : 15000;
+            if (cfg->signer.timeout_ms <= 0) cfg->signer.timeout_ms = 15000;
+
+            fprintf(stderr, "  Checking connectivity to n_signer...\n");
+#if defined(NOSTR_ENABLE_NSIGNER_CLIENT)
+            nostr_signer_t* signer = nostr_signer_nsigner_unix(cfg->signer.socket_name[0] ? cfg->signer.socket_name : NULL,
+                                                               cfg->signer.role,
+                                                               cfg->signer.timeout_ms);
+            if (!signer) {
+                fprintf(stderr, "%sFailed to initialize n_signer client.%s\n", ANSI_RED, ANSI_RESET);
+                continue;
+            }
+            if (nostr_signer_get_public_key(signer, cfg->keys.public_key_hex) != 0) {
+                fprintf(stderr, "%sFailed to retrieve public key from n_signer.%s\n", ANSI_RED, ANSI_RESET);
+                nostr_signer_free(signer);
+                continue;
+            }
+            nostr_signer_free(signer);
+            fprintf(stderr, "%sConnectivity check: OK. Pubkey: %s%s\n", ANSI_YELLOW, cfg->keys.public_key_hex, ANSI_RESET);
+#else
+            fprintf(stderr, "%sThis build was compiled without n_signer client support (NOSTR_ENABLE_NSIGNER_CLIENT). Connectivity check skipped; the agent will fail at startup in this mode.%s\n",
+                    ANSI_RED, ANSI_RESET);
+#endif
+        }
+
         return 0;
     }
 }

src/signer_health.c

@@ -0,0 +1,132 @@
+#define _POSIX_C_SOURCE 200809L
+
+#include "signer_health.h"
+
+#include <stdio.h>
+#include <string.h>
+#include <pthread.h>
+
+#include "../nostr_core_lib/nostr_core/nostr_common.h"
+
+static pthread_mutex_t g_lock = PTHREAD_MUTEX_INITIALIZER;
+static signer_health_state_t g_state = SIGNER_HEALTH_UNKNOWN;
+static char g_mode[32] = {0};
+static char g_last_reason[SIGNER_HEALTH_REASON_LEN] = {0};
+static time_t g_last_error_ts = 0;
+static time_t g_last_ok_ts = 0;
+
+void signer_health_set_mode(const char* mode) {
+    pthread_mutex_lock(&g_lock);
+    if (mode && mode[0]) {
+        snprintf(g_mode, sizeof(g_mode), "%s", mode);
+    } else {
+        g_mode[0] = '\0';
+    }
+    pthread_mutex_unlock(&g_lock);
+}
+
+void signer_health_reset(void) {
+    pthread_mutex_lock(&g_lock);
+    g_state = SIGNER_HEALTH_UNKNOWN;
+    g_mode[0] = '\0';
+    g_last_reason[0] = '\0';
+    g_last_error_ts = 0;
+    g_last_ok_ts = 0;
+    pthread_mutex_unlock(&g_lock);
+}
+
+/* Classify a nostr error code into a short category label used both for
+ * the health reason string and for log clarity. The categories map to
+ * the failure modes called out in Phase 4 item 18:
+ *   transport/IO  - network or socket failure talking to n_signer
+ *   auth/policy   - n_signer rejected the request (auth envelope, policy)
+ *   crypto        - the signer performed work but the crypto op failed
+ *                   (e.g. decrypt of malformed ciphertext). This is NOT
+ *                   necessarily a signer outage, but we still record it
+ *                   so the operator can see recent signer activity.
+ *   unknown       - anything else.
+ *
+ * Note: nostr_core_lib does not currently expose dedicated nsigner
+ * transport/auth error codes; remote signer failures surface as
+ * NOSTR_ERROR_IO_FAILED / NOSTR_ERROR_NETWORK_FAILED (transport) or
+ * NOSTR_ERROR_CRYPTO_FAILED (the nsigner client maps server-side
+ * rejections to crypto-failed when it cannot be more specific). We
+ * treat IO/network as the strong "signer unreachable" signal. */
+static const char* classify_rc(int rc) {
+    if (rc == NOSTR_ERROR_IO_FAILED || rc == NOSTR_ERROR_NETWORK_FAILED) {
+        return "transport/IO";
+    }
+    if (rc == NOSTR_ERROR_CRYPTO_FAILED) {
+        return "crypto/auth";
+    }
+    if (rc == NOSTR_ERROR_MEMORY_FAILED) {
+        return "resource";
+    }
+    if (rc == NOSTR_ERROR_INVALID_INPUT) {
+        return "invalid-input";
+    }
+    return "unknown";
+}
+
+void signer_health_record_ok(void) {
+    int transitioned_from_unhealthy = 0;
+    pthread_mutex_lock(&g_lock);
+    time_t now = time(NULL);
+    if (g_state == SIGNER_HEALTH_UNHEALTHY) {
+        transitioned_from_unhealthy = 1;
+    }
+    g_state = SIGNER_HEALTH_HEALTHY;
+    g_last_ok_ts = now;
+    /* Keep last_reason/last_error_ts so the operator can see the most
+     * recent prior failure even after recovery. */
+    pthread_mutex_unlock(&g_lock);
+
+    if (transitioned_from_unhealthy) {
+        fprintf(stderr,
+                "[didactyl] signer health transition: unhealthy -> healthy (mode=%s)\n",
+                g_mode[0] ? g_mode : "local");
+    }
+}
+
+void signer_health_record_failure(int nostr_rc, const char* detail) {
+    int transitioned_from_healthy = 0;
+    char reason[SIGNER_HEALTH_REASON_LEN];
+    const char* cls = classify_rc(nostr_rc);
+    if (detail && detail[0]) {
+        snprintf(reason, sizeof(reason), "%s: %s (rc=%d)", cls, detail, nostr_rc);
+    } else {
+        snprintf(reason, sizeof(reason), "%s (rc=%d)", cls, nostr_rc);
+    }
+
+    pthread_mutex_lock(&g_lock);
+    time_t now = time(NULL);
+    if (g_state == SIGNER_HEALTH_HEALTHY) {
+        transitioned_from_healthy = 1;
+    }
+    g_state = SIGNER_HEALTH_UNHEALTHY;
+    snprintf(g_last_reason, sizeof(g_last_reason), "%s", reason);
+    g_last_error_ts = now;
+    pthread_mutex_unlock(&g_lock);
+
+    if (transitioned_from_healthy) {
+        fprintf(stderr,
+                "[didactyl] signer health transition: healthy -> unhealthy "
+                "(mode=%s, reason=%s)\n",
+                g_mode[0] ? g_mode : "local",
+                reason);
+    }
+}
+
+int signer_health_snapshot(signer_health_snapshot_t* out) {
+    if (!out) {
+        return -1;
+    }
+    pthread_mutex_lock(&g_lock);
+    out->state = g_state;
+    snprintf(out->mode, sizeof(out->mode), "%s", g_mode);
+    snprintf(out->last_reason, sizeof(out->last_reason), "%s", g_last_reason);
+    out->last_error_ts = g_last_error_ts;
+    out->last_ok_ts = g_last_ok_ts;
+    pthread_mutex_unlock(&g_lock);
+    return 0;
+}

src/signer_health.h

@@ -0,0 +1,59 @@
+#ifndef DIDACTYL_SIGNER_HEALTH_H
+#define DIDACTYL_SIGNER_HEALTH_H
+
+#include <time.h>
+
+/* Signer runtime health tracking (Phase 4 item 18/19).
+ *
+ * Lightweight process-global state recording whether the active signer
+ * provider (local or remote n_signer) is currently considered healthy,
+ * along with the last error reason and timestamp. This is surfaced via
+ * the HTTP /api/status endpoint so an operator can detect a signing
+ * outage out-of-band (without requiring a signed admin DM to come back).
+ *
+ * The state is intentionally minimal and lock-protected; it is updated
+ * from central signer call paths (nostr_handler self-encrypt/decrypt,
+ * DM encrypt/decrypt, main.c startup connectivity check). It is NOT a
+ * full health-check daemon: it reflects the outcome of the last signer
+ * operation that was attempted.
+ */
+
+typedef enum {
+    SIGNER_HEALTH_UNKNOWN = 0,   /* no signer operation attempted yet */
+    SIGNER_HEALTH_HEALTHY = 1,
+    SIGNER_HEALTH_UNHEALTHY = 2
+} signer_health_state_t;
+
+#define SIGNER_HEALTH_REASON_LEN 256
+
+typedef struct {
+    signer_health_state_t state;
+    char mode[32];                                  /* snapshot of cfg.signer.mode */
+    char last_reason[SIGNER_HEALTH_REASON_LEN];     /* human-readable last error */
+    time_t last_error_ts;                           /* unix ts of last unhealthy transition */
+    time_t last_ok_ts;                              /* unix ts of last healthy observation */
+} signer_health_snapshot_t;
+
+/* Record the configured signer mode at startup. Call once after the
+ * signer is constructed. Safe to call multiple times. */
+void signer_health_set_mode(const char* mode);
+
+/* Mark the signer healthy and record a successful operation timestamp.
+ * Emits a one-line warning if this is a transition from unhealthy -> healthy. */
+void signer_health_record_ok(void);
+
+/* Mark the signer unhealthy with a reason string and the nostr error code
+ * (from nostr_common.h). The reason is formatted as "<classification>: <detail>".
+ * Emits a one-line warning if this is a transition from healthy -> unhealthy.
+ * Pass rc=0 only if you do not have a nostr error code (the detail string
+ * should then fully describe the failure). */
+void signer_health_record_failure(int nostr_rc, const char* detail);
+
+/* Thread-safe snapshot copy for the HTTP status endpoint. Returns 0 on
+ * success, -1 if out is NULL. */
+int signer_health_snapshot(signer_health_snapshot_t* out);
+
+/* Reset state (used by tests / reinit). */
+void signer_health_reset(void);
+
+#endif /* DIDACTYL_SIGNER_HEALTH_H */

src/tools/tool_blossom.c

@@ -117,12 +117,26 @@ char* execute_blossom_upload(tools_context_t* ctx, const char* args_json) {
     }
 
     blossom_blob_descriptor_t d;
-    int rc = blossom_upload_file(server->valuestring,
+    /* Phase 3 item 16: route the Blossom upload auth/signature through the
+     * process signer when wired into the tools context so remote signer modes
+     * keep the nsec out of the agent. Falls back to the legacy raw-key path
+     * when the signer is NULL (local mode / pre-Phase-3). */
+    int rc;
+    if (ctx->signer) {
+        rc = blossom_upload_file_with_signer(server->valuestring,
+                                             full_path,
+                                             (content_type && cJSON_IsString(content_type) && content_type->valuestring) ? content_type->valuestring : NULL,
+                                             ctx->signer,
+                                             30,
+                                             &d);
+    } else {
+        rc = blossom_upload_file(server->valuestring,
                                  full_path,
                                  (content_type && cJSON_IsString(content_type) && content_type->valuestring) ? content_type->valuestring : NULL,
                                  ctx->cfg->keys.private_key,
                                  30,
                                  &d);
+    }
     cJSON_Delete(args);
     if (rc != NOSTR_SUCCESS) return json_error_local("blossom_upload failed");
 
@@ -235,7 +249,16 @@ char* execute_blossom_delete(tools_context_t* ctx, const char* args_json) {
         return json_error_local("blossom_delete requires an https:// server URL");
     }
 
-    int rc = blossom_delete(server->valuestring, sha->valuestring, ctx->cfg->keys.private_key, 15);
+    /* Phase 3 item 16: route the Blossom delete auth/signature through the
+     * process signer when wired into the tools context so remote signer modes
+     * keep the nsec out of the agent. Falls back to the legacy raw-key path
+     * when the signer is NULL (local mode / pre-Phase-3). */
+    int rc;
+    if (ctx->signer) {
+        rc = blossom_delete_with_signer(server->valuestring, sha->valuestring, ctx->signer, 15);
+    } else {
+        rc = blossom_delete(server->valuestring, sha->valuestring, ctx->cfg->keys.private_key, 15);
+    }
     cJSON_Delete(args);
     if (rc != NOSTR_SUCCESS) return json_error_local("blossom_delete failed");
 

src/tools/tool_config.c

@@ -37,6 +37,20 @@ static int nip44_encrypt_self_local(tools_context_t* ctx, const char* plaintext,
     if (!ctx || !ctx->cfg || !out_ciphertext) return -1;
 
     const char* plain = plaintext ? plaintext : "";
+
+    /* Phase 3 item 13: route self-encrypt through the process signer when
+     * wired into the tools context. Falls back to the legacy raw-key path. */
+    if (ctx->signer) {
+        char* signer_out = NULL;
+        int rc = nostr_signer_nip44_encrypt(ctx->signer,
+                                            ctx->cfg->keys.public_key_hex,
+                                            plain,
+                                            &signer_out);
+        if (rc != NOSTR_SUCCESS || !signer_out) return -1;
+        *out_ciphertext = signer_out;
+        return 0;
+    }
+
     size_t out_cap = (strlen(plain) * 4U) + 1024U;
     char* ciphertext = (char*)malloc(out_cap);
     if (!ciphertext) return -1;
@@ -58,6 +72,19 @@ static int nip44_encrypt_self_local(tools_context_t* ctx, const char* plaintext,
 static int nip44_decrypt_self_local(tools_context_t* ctx, const char* ciphertext, char** out_plaintext) {
     if (!ctx || !ctx->cfg || !ciphertext || !out_plaintext) return -1;
 
+    /* Phase 3 item 13: route self-decrypt through the process signer when
+     * wired into the tools context. Falls back to the legacy raw-key path. */
+    if (ctx->signer) {
+        char* signer_out = NULL;
+        int rc = nostr_signer_nip44_decrypt(ctx->signer,
+                                            ctx->cfg->keys.public_key_hex,
+                                            ciphertext,
+                                            &signer_out);
+        if (rc != NOSTR_SUCCESS || !signer_out) return -1;
+        *out_plaintext = signer_out;
+        return 0;
+    }
+
     size_t out_cap = strlen(ciphertext) + 1024U;
     char* plaintext = (char*)malloc(out_cap);
     if (!plaintext) return -1;