Copilot Babysitter Skill

Purpose

Monitor the VS Code GitHub Copilot Agent and automatically nudge it to continue when it stalls, stops reporting progress, or waits unnecessarily for user input.

Key capability: Works through macOS screen lock — no need to keep the screen unlocked.

Design philosophy: semantic judgment, not fixed states

Copilot going silent is not one state — it can mean very different things, and each needs the opposite response:

The babysitter is smart enough to make routine engineering decisions on Roie's behalf. It must NOT bounce every "should I continue?" question to Roie — that just recreates the stall. It answers routine questions itself (approving Copilot's own recommendation, or using obvious engineering sense like "validate before refactoring" / "fix the blocker first" / "prove the pattern early") and tells Copilot to proceed autonomously. It only escalates to Roie for genuinely human matters: secrets/credentials, destructive or irreversible actions (deleting prod, force-push, spending money, notifying external people), external actions the agent can't perform, or a real trade-off where guessing wrong is costly.

Older versions used rigid keyword/state rules (ONLY_MESSAGE_ON_USER_INPUT, wait, etc.) that lumped done / working / stuck all under "idle" and stayed silent for all of them — so a Copilot that falsely believed it was "monitoring a deploy" (but had actually done nothing for hours) slipped through unnoticed.

The current design instead hands the raw conversation to the LLM automation, which reads it and reasons about why Copilot went quiet. The supervisor.py script is a dumb sensor + actuator; the LLM is the brain:

• supervisor.py context → emits a rich LLM-ready snapshot (no decision made).
• supervisor.py nudge "<msg>" → sends an LLM-authored, context-specific message.

The deterministic once / monitor paths still exist for backward compatibility, but the recommended flow is the semantic one below.

Setup (One-Time)

Prerequisites

• macOS
• VS Code with GitHub Copilot extension
• Clawpilot (for automation scheduling)

Install the copilot-nudge-server Extension

The babysitter relies on a small VS Code extension that runs an HTTP server inside VS Code's extension host process. This allows sending messages to Copilot Chat evenprogrammatically when the screen is locked.

Install steps:

1. Copy the extension to VS Code's extensions folder:

   mkdir -p ~/.vscode/extensions/copilot-nudge-server-0.0.1
   cp extension/extension.js ~/.vscode/extensions/copilot-nudge-server-0.0.1/
   cp extension/package.json ~/.vscode/extensions/copilot-nudge-server-0.0.1/

"Developer: Reload Window")

3. Verify the extension is running:

   curl -s http://127.0.0.1:19876/health
   # Expected: {"status":"ok","port":19876,"version":2}

Why this works through screen lock:

• The extension runs as a Node.js HTTP server inside VS Code's extension host process
• It uses internal VS Code commands (workbench.action.chat. no keyboard/UI injectionopen)
• The HTTP server stays active regardless of display sleep or screen lock state
• Messages are queued by Copilot when the agent is busy; processed in order when ready

Register the Automation in Clawpilot

Create a Clawpilot automation that runs every 2 minutes:

• Name: "Copilot Agent Monitor"
• Schedule: "every 2 minutes"
• Prompt: (see the automation prompt template in this skill)

Architecture (Clawpilot Automation Mode)

The babysitter runs as a Clawpilot automation (every 2 minutes). Each run:

1. Check stat -f "%m" on the session file vs current timestaleness
2. If active (< no action needed, report OK90s)
3. If stalled (> diagnose and nudge:90s) a. Try HTTP nudge first (works through screen lock) b. If HTTP fails, check screen lock status c. Read session context for what agent was doing d. Determine if agent needs nudge or hit real blocker e. Send contextual nudge OR alert Roie via Teams
4. Post-nudge 60s after nudge, re-check timestamp changedverification

Screen Lock Handling

Problem: When macOS screen is locked, all UI automation (osascript keystrokes) silently text goes to the lock screen password field. osascript still returns exit 0.fails

Solution: The HTTP nudge bypasses this entirely. The decision tree is:

1. Try HTTP nudge (curl POST to :19876)
 done (works through screen lock!)

      2. Check screen lock (ioreg)
 Teams alert only, cannot nudge via UI
 try UI nudge (osascript fallback)

Screen lock detection:

ioreg -n Root -d1 -w0 | grep -q '"IOConsoleLocked" = Yes'
# Exit 0 = screen IS locked, Exit 1 = screen is unlocked

Nudge Methods

PRIMARY: HTTP (Non-UI, Works Through Screen Lock)

curl -s -X POST http://127.0.0.1:19876/nudge \
  -H "Content-Type: application/json" \
  -d '{"message": "YOUR_MESSAGE"}'

Health check (verify extension is running):

curl -s http://127.0.0.1:19876/health
# Returns: {"status":"ok","port":19876,"version":2}

File-based alternative (if HTTP unreachable):

echo 'YOUR_MESSAGE' > ~/.copilot/nudge-queue.txt

The extension polls this file every 2 seconds.

FALLBACK: UI (Only When HTTP Fails AND Screen Unlocked)

tell application "Code" to activate
delay 0.5
tell application "System Events"
    tell process "Code"
        key code 35 using {command down, shift down}  -- Cmd+Shift+P
        delay 0.5
        keystroke "chat focus input"
        delay 0.3
        keystroke return
        delay 0.4
        keystroke "YOUR_MESSAGE_HERE"
        delay 0.2
        keystroke return
    end tell
end tell

Session File Monitoring

Target session (update these for your workspace):

• Workspace hash: 680f52b117f3c92a8c4998a69b70dacc
• Session ID: 3df56667-99c5-4383-ac30-7acb02f89aa9
• Full path: ~/Library/Application Support/Code/User/workspaceStorage/{hash}/chatSessions/{sessionId}.jsonl

Staleness check:

stat -f "%m" "$SESSION_FILE" && date +%s
 stalled

Auto-Nudge Policy (semantic)

The LLM automation reasons over supervisor.py context and acts only when needed:

1. Working / Done → do nothing (stay silent).
2. Stuck → send ONE tailored nudge via supervisor.py nudge "<msg>". The command enforces MAX_NUDGES (default 5) consecutive nudges and records state.
3. Already nudged, no reaction yet (nudged_since_last_activity: true) → wait one cycle; do not double-nudge.
4. Nudge counter auto-resets the moment Copilot writes to the session after a nudge (it reacted), so a fresh stall later starts from zero.
5. After MAX_NUDGES with no progress → back off and alert Roie via Teams.
6. Routine question ("shall I proceed?", "which order?", "want me to fix X now?", or Copilot already gave a recommendation) → answer it yourself and nudge with the decision. Approve Copilot's recommendation, or use obvious engineering sense (validate before refactoring, fix the blocker first, prove the pattern early). Also tell Copilot to keep going autonomously and stop only for genuinely human matters — not just to ask permission to continue.
7. Needs a real human → do NOT nudge; notify Roie via Teams. Reserve this for: a secret/credential/OTP only Roie has; a destructive or irreversible action (delete prod, force-push, spend money, notify external people); an external/manual action the agent can't perform; or a costly trade-off with no clear best option.

Answering routine questions is the default, not the exception. Bouncing every "should I continue?" back to Roie recreates the very stall the babysitter exists to prevent. The nudge message should state the decision clearly (which option / what order / "yes, proceed"), a brief why, and instruct Copilot to continue autonomously.

Detecting a false "still working" claim — treat as stuck when Copilot says things like "I'll ping you when it clears", "I'll report at the next milestone", or "still building", but has been idle a long time (background agents CANNOT self-resume — once the turn ends Copilot waits forever), or it repeats the same "same phase as last check" status across turns with no new tool activity. When in doubt between working and stuck, treat as stuck.

Nudge messages must be contextual — read what the agent was doing and tell it exactly what to do next. For an abandoned background/deploy watch: instruct it to re-check NOW (tail the log, grep for errors, pgrep the process, verify real state directly via az/kubectl), decide whether the job finished/failed/stalled, then proceed or fix. Do NOT just send "continue".

Teams Status Updates

Only message Roie for genuine human-in-the-loop blockers or after max-nudge back-off — keep it to 1-2 lines with the session title and the exact thing Copilot is waiting for. Do not send routine "still working" status pings.

Helper Tools

supervisor.py commands

# Rich LLM-ready snapshot (idle time, mission, last response, tool states,
# nudge bookkeeping). Makes NO decision — the LLM reasons over this.
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py context

# Send an LLM-authored message to Copilot chat (respects MAX_NUDGES; --force overrides).
# Prefer piping via stdin (heredoc) so backticks, $(...), quotes, or ! in the message
# are NOT interpreted by the shell:
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py nudge <<'NUDGE_EOF'
your tailored message here
NUDGE_EOF
# (An inline arg also works for simple messages: supervisor.py nudge "message")

# Clear the consecutive-nudge counter (e.g. after the user intervenes manually).
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py reset

# Keep-awake: ensure a detached `caffeinate` keeps the Mac from idle-sleeping
# so the every-2-minute monitor never stalls. Idempotent. This is invoked
# AUTOMATICALLY on every `context` call, so normally you never run it by hand.
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py keepawake
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py stopawake   # stop it

# Legacy/diagnostic:
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py status
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py read 3
python3 ~/.copilot/skills/copilot-babysitter/supervisor.py once     # deterministic one-shot

The context snapshot includes nudged_since_last_activity and nudge_count so the LLM can avoid double-nudging and knows when to back off. It also includes a keepawake field (started / already-running / skipped) confirming the anti-sleep guard is active.

Keeping the machine awake (anti-sleep)

Scheduled automations only fire while the Mac is awake and the app is running — a sleeping machine silently skips 2-minute ticks (this caused a ~1h monitoring gap once). To prevent idle-sleep, supervisor.py context automatically ensures a detached caffeinate -dimsu process is running (tracked via ~/.copilot/copilot-supervisor-caffeinate.pid, idempotent, macOS-only). No manual step is needed.

Caveat — clamshell (lid-closed) sleep: caffeinate does NOT prevent a MacBook from sleeping when the lid is closed on battery. For that, additionally run (needs admin/password):

sudo pmset -a disablesleep 1     # prevent lid-close sleep
sudo pmset -a disablesleep 0     # re-enable normal sleep later

Requirements

Known Limitations

• If VS Code crashes or reloads, extension reactivates automatically on next startup
• Session file can be very large ( too big to parse last line efficiently300MB+)
• osascript returns exit 0 even when keystrokes fail (UI fallback only)
• Extension uses port 19876; if port is taken it tries 19877
• Anti-sleep caffeinate cannot prevent lid-closed (clamshell) sleep on battery — use sudo pmset -a disablesleep 1 for that

Extension Source

The extension source is in extension/ in this repo. See extension/extension.js and extension/package.json.