claudetools/projects/discord-bot/session-logs/2026-05-20-session.md

Discord Bot — Instruction Corrections — 2026-05-20

User

• User: Mike Swanson (mike)
• Machine: GURU-BEAST-ROG
• Role: admin

Session Summary

The session began with a repository sync, pulling 41 commits initially and 9 additional commits mid-session, including the Cascades-Tucson migration phase 2.6 work, M365 offboarding for britney.thompson, a new /forum-post command, and a fix to the check-messages.sh hook path. The SOPS vault was also synced (MSP360 Managed Backup API credentials added in a prior session). The Discord bot operating instructions were reviewed and internalized, then the ClaudeToolsDiscordBot Windows service was restarted so the newly pulled bot code and rules took effect.

Following a user request to correct the bot's behavior, the bot architecture was investigated by reading bot/config.py, bot/claude/client.py, and bot/handlers/message_handler.py. This revealed that DISCORD_CLAUDE.md is the agent system_prompt, loaded ONCE at bot startup (ClaudeAgentManager.__init__ -> _load_system_prompt), and that each Discord thread is a persistent ClaudeSDKClient session kept in self._agents[thread_id]. Multi-turn back-and-forth was therefore already supported by the architecture — the prior "single turn / never ask questions" rule was an unnecessary self-restriction, not a real limitation.

Three edits were made to DISCORD_CLAUDE.md to reverse the no-interaction rule, add a headless-operation constraint, and define a structured task loop. Because the system prompt loads only at startup, the bot service was restarted to load the corrected instructions; reconnection to the Arizona Computer Guru guild was confirmed with a clean stderr.

Key Decisions

• Reversed the no-interaction rule. The bot may and should ask clarifying questions in plain text. Rationale: the thread is a persistent session, so a follow-up message continues the same conversation with full context — asking costs nothing and prevents wrong guesses on consequential actions. The AskUserQuestion tool is explicitly excluded because it does not render in Discord.
• Added a "You Are Headless" constraint. The bot runs as a background Windows service with no human at the BEAST console, so any GUI/interactive prompt (Chrome/browser, OAuth sign-in window, Windows credential prompt, UAC dialog, 1Password/SOPS GUI unlock) would hang forever. The bot must pull credentials non-interactively from the SOPS vault, or ask the requester to perform the interactive step on their own machine and report back.
• Introduced a Task Loop. Standardized flow: identify the requester from [DISCORD_CONTEXT] -> do the work (asking questions as needed) -> ask "anything else?" -> offer to log in Syncro (/syncro) -> /save. The "After Every Completed Task" section was updated to match (now records whether a Syncro ticket was created/updated).

Problems Encountered

• None. Both bot restarts succeeded and the service reconnected cleanly each time.

Configuration Changes

Files modified:

• projects/discord-bot/DISCORD_CLAUDE.md — 3 edits (+52 / -17):
  1. Intro paragraph: replaced "single turn / no back-and-forth loop" with persistent-session framing.
  2. Replaced ## CRITICAL: No Interactive Interaction with two sections: ## You Can — and Should — Ask Questions and ## CRITICAL: You Are Headless — No One Is at BEAST, plus a new ## Task Loop section.
  3. Updated ## After Every Completed Task to reference the loop and the Syncro ticket field.

No code files were changed. No vault files or .claude/identity.json touched.

Commands & Outputs

• nssm restart ClaudeToolsDiscordBot — run twice (first after the start-of-session sync to load pulled bot code; second after editing the instructions). Both: STOP + START succeeded, service Running.
• Post-restart verification (second restart): stdout showed guild channel enumeration at 2026-05-20 16:19:04 (the bot "ready" sequence); stderr empty.

Infrastructure & Services

• Machine: GURU-BEAST-ROG (BEAST) — Windows 11 Pro
• Service: ClaudeToolsDiscordBot (NSSM, StartType Automatic), runs the Discord bot
• nssm: C:\Users\guru\AppData\Local\Microsoft\WinGet\Links\nssm.exe
• Bot working dir / agent cwd: C:/Users/guru/ClaudeTools
• Bot model: claude-sonnet-4-6 (per bot/config.py)
• Bot logs: projects/discord-bot/logs/stdout.log, stderr.log
• Discord guild: Arizona Computer Guru (id 624663750603046913), 11 channels

Credentials

• None used, discovered, or changed this session. The bot authenticates via its Discord token (in projects/discord-bot/.env, gitignored) and either the local Claude Code OAuth credential or ANTHROPIC_API_KEY; none were read or modified here.

Reference Information

• Bot architecture (verified this session):
  • System prompt source: projects/discord-bot/DISCORD_CLAUDE.md (config key discord_system_prompt, relative to claudetools_root)
  • Loaded ONCE at startup in ClaudeAgentManager.__init__ -> client.py:_load_system_prompt() — editing it requires a bot restart to take effect
  • One persistent ThreadAgent (ClaudeSDKClient) per Discord thread_id; follow-up messages reuse the same client, preserving conversation history
  • Caller identity injected as [DISCORD_CONTEXT] header in message_handler.py
• Restart command: nssm restart ClaudeToolsDiscordBot

Pending / Next Steps

• None outstanding for the bot. New rules are live as of the 16:19 restart.
• Untracked pre-existing items in the repo (NOT part of this session, left as-is): clients/internal-infrastructure/datto-bsod-case-2026-05-16*, clients/valleywide/app-modernization/source-analysis/D-drive-*.csv.