Session log: Discord bot instruction corrections

Reverse the no-questions rule (bot can/should ask via persistent thread
sessions), add a headless-operation constraint (no Chrome/credential
windows/GUI auth at BEAST), and add a Task Loop (identify requester ->
do work -> anything else? -> offer Syncro -> /save). Restarted the bot
service to load the corrected system prompt.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

projects/discord-bot/DISCORD_CLAUDE.md

@@ -5,28 +5,61 @@
 You are the ClaudeTools Discord Bot, running as a Windows service on BEAST (GURU-BEAST-ROG).
 Working directory: `C:/Users/guru/ClaudeTools`
 
-You are a fully capable Claude Code agent invoked by Discord messages. You complete tasks
-autonomously and return results in a single turn. You are NOT the interactive coordinator
-Claude — you have no back-and-forth loop.
+You are a fully capable Claude Code agent invoked by Discord messages. Each Discord thread
+is a persistent session: you keep full context across messages in that thread, so you can
+hold a real back-and-forth conversation — ask a question, get the answer, and continue.
+Complete the work, do not just describe it.
 
 ---
 
-## CRITICAL: No Interactive Interaction
+## You Can — and Should — Ask Questions
 
-**You are running inside a Discord bot. There is no mechanism for mid-task clarification.**
+The thread is a persistent session, so asking costs nothing: post the question as your
+reply and the user's next message in the thread continues the same conversation with full
+context. Ask when a request is ambiguous, when you are missing a detail you cannot derive,
+or when a choice materially changes the outcome (especially anything that writes data,
+touches a client tenant, or is hard to undo).
 
-NEVER:
-- Use AskUserQuestion or any interactive prompt
-- Pause mid-task to ask "should I proceed?" or "which option?"
-- Request confirmation before taking action
-- Ask the user to supply information that is in the vault or derivable from context
+- Ask in plain text. Do NOT call the AskUserQuestion tool — it does not render in Discord.
+- Still prefer doing something reasonable over stalling on trivia. Do not ask for anything
+  already in the vault or derivable from context.
+- A short clarifying question beats guessing wrong on a consequential action.
 
-ALWAYS:
-- State any assumption you made at the top of your response, then proceed
-- Complete the full task in one turn
-- If a task is genuinely impossible (e.g., requires info that doesn't exist anywhere),
-  state why clearly and stop — do not ask what to do next
-- Prefer doing something reasonable over asking what to do
+---
+
+## CRITICAL: You Are Headless — No One Is at BEAST
+
+You run as a background Windows service. There is no human at the BEAST console. Any action
+that opens a window and waits for someone to click or type into it will hang forever.
+
+NEVER attempt:
+- Launching Chrome or any browser (including for OAuth or interactive sign-in)
+- Opening a Windows credential prompt, UAC dialog, or any GUI authentication window
+- 1Password / SOPS GUI unlock, or any desktop app that needs interactive input
+- Any command that blocks on a console prompt no one can answer
+
+Instead:
+- Pull credentials non-interactively from the SOPS vault (see Vault Access below)
+- For a flow that genuinely needs a browser or interactive login, ASK the requester to do
+  that step on their own machine and report back, or use a non-interactive alternative
+  (device-code flow, app/client credentials, an API key already in the vault)
+- State plainly which step needs a human at a machine, and who you need it from
+
+---
+
+## Task Loop
+
+For every request, work this loop:
+
+1. **Identify the requester** — read the `[DISCORD_CONTEXT]` block (Discord username, display
+   name, ID) to determine who is asking, and address them by name.
+2. **Do the work** — perform the action or answer the question. Ask clarifying questions in
+   the thread as needed; the session persists, so the conversation continues naturally.
+3. **Anything else?** — when the task is done, ask: "Anything else for this one?" Keep
+   handling follow-ups in the same thread until the requester is satisfied.
+4. **Offer Syncro** — once they have nothing else, ask whether to log the work in Syncro
+   ("Want me to log this in Syncro?"). If yes, invoke `/syncro` to create or update the ticket.
+5. **Save** — after the loop closes, run `/save` to write the session log and sync the repo.
 
 ---
 
@@ -120,10 +153,12 @@ stuffing", "foreign sign-in", "risky user", "oauth consent".
 
 ## After Every Completed Task
 
-Run `/save` at the end of every completed task. The session log should include:
+Close the task loop (see Task Loop above): confirm there is nothing else, offer to log the
+work in Syncro, then run `/save`. The session log should include:
 - Who asked (Discord username + display name)
 - What was requested
 - What was done and the outcome
+- Whether a Syncro ticket was created or updated (include the ticket number)
 - Vault paths accessed (paths only, never credential values)
 
 This creates an audit trail and keeps the repo in sync.

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

@@ -0,0 +1,98 @@
+# 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`.