chore: prepare overnight automation 2026-03-03

Update loop scripts with rate limit handling, set plan for tonight's
run, and update prompt.md with task instructions.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

loop/loop.sh

@@ -1,6 +1,7 @@
 #!/usr/bin/env sh
 # Headless loop script for overnight Claude Code automation.
 # Set CLAUDE_AUTONOMOUS=1 for Ralph Wiggum (Stop hook blocks until plan is complete).
+# Rate-limit aware: detects limits, sleeps until reset, and retries automatically.
 set -eu
 
 PROJECT_DIR="${CLAUDE_PROJECT_DIR:-$(cd "$(dirname "$0")/.." && pwd)}"
@@ -9,18 +10,43 @@ LOG_FILE="${LOG_FILE:-$PROJECT_DIR/loop/loop.log}"
 ITERATION_COUNT="${ITERATION_COUNT:-1}"
 ITERATION_DELAY="${ITERATION_DELAY:-600}"
 CLAUDE_BIN="${CLAUDE_BIN:-claude}"
+RATE_LIMIT_WAIT="${RATE_LIMIT_WAIT:-3600}"  # Default: wait 1 hour on rate limit
+MAX_RATE_LIMIT_RETRIES="${MAX_RATE_LIMIT_RETRIES:-5}"  # Max retries before giving up
 
 cd "$PROJECT_DIR"
 
-echo "=== Overnight loop started $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ===" | tee -a "$LOG_FILE"
-echo "  PROMPT_FILE=$PROMPT_FILE" | tee -a "$LOG_FILE"
-echo "  CLAUDE_AUTONOMOUS=${CLAUDE_AUTONOMOUS:-0}" | tee -a "$LOG_FILE"
-echo "  ITERATION_COUNT=$ITERATION_COUNT" | tee -a "$LOG_FILE"
-echo "" | tee -a "$LOG_FILE"
+log() {
+  echo "$1" | tee -a "$LOG_FILE"
+}
+
+# Check if plan has remaining tasks
+plan_has_tasks() {
+  grep -q '^\- \[ \]' "$PROJECT_DIR/loop/plan.md" 2>/dev/null
+}
+
+# Detect rate limit from Claude output
+check_rate_limit() {
+  # Check last 50 lines of log for rate limit indicators
+  tail -50 "$LOG_FILE" 2>/dev/null | grep -qi \
+    -e "rate.limit" \
+    -e "too.many.requests" \
+    -e "429" \
+    -e "quota.exceeded" \
+    -e "usage.limit" \
+    -e "limit.reached" 2>/dev/null
+}
+
+log "=== Overnight loop started $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ==="
+log "  PROMPT_FILE=$PROMPT_FILE"
+log "  CLAUDE_AUTONOMOUS=${CLAUDE_AUTONOMOUS:-0}"
+log "  ITERATION_COUNT=$ITERATION_COUNT"
+log "  RATE_LIMIT_WAIT=${RATE_LIMIT_WAIT}s"
+log ""
 
 i=1
+rate_limit_retries=0
 while [ "$i" -le "$ITERATION_COUNT" ]; do
-  echo "--- Iteration $i/$ITERATION_COUNT @ $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ---" | tee -a "$LOG_FILE"
+  log "--- Iteration $i/$ITERATION_COUNT @ $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ---"
   export CLAUDE_PROJECT_DIR="$PROJECT_DIR"
   export CLAUDE_AUTONOMOUS="${CLAUDE_AUTONOMOUS:-1}"
 
@@ -29,15 +55,88 @@ while [ "$i" -le "$ITERATION_COUNT" ]; do
     "$CLAUDE_BIN" -p --dangerously-skip-permissions --output-format=stream-json \
       < "$PROMPT_FILE" 2>&1 | tee -a "$LOG_FILE" || true
   else
-    echo "Error: $PROMPT_FILE not found" | tee -a "$LOG_FILE"
+    log "Error: $PROMPT_FILE not found"
     exit 1
   fi
 
+  # Check for rate limit after Claude exits
+  if check_rate_limit; then
+    rate_limit_retries=$((rate_limit_retries + 1))
+    if [ "$rate_limit_retries" -ge "$MAX_RATE_LIMIT_RETRIES" ]; then
+      log "Rate limited $rate_limit_retries times — giving up."
+      log "Scheduling retry via launchd..."
+
+      # Schedule a retry using launchd for after rate limit resets
+      PLIST_LABEL="com.aiui.overnight-retry"
+      PLIST_PATH="$HOME/Library/LaunchAgents/${PLIST_LABEL}.plist"
+      RETRY_TIME=$(date -v+${RATE_LIMIT_WAIT}S '+%H:%M' 2>/dev/null || date -d "+${RATE_LIMIT_WAIT} seconds" '+%H:%M')
+      RETRY_HOUR=$(echo "$RETRY_TIME" | cut -d: -f1)
+      RETRY_MIN=$(echo "$RETRY_TIME" | cut -d: -f2)
+
+      cat > "$PLIST_PATH" <<PLIST
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+  <key>Label</key>
+  <string>${PLIST_LABEL}</string>
+  <key>ProgramArguments</key>
+  <array>
+    <string>/bin/sh</string>
+    <string>-c</string>
+    <string>cd ${PROJECT_DIR} && caffeinate -i ./loop/loop.sh >> ${LOG_FILE} 2>&1; launchctl unload ${PLIST_PATH}; rm -f ${PLIST_PATH}</string>
+  </array>
+  <key>StartCalendarInterval</key>
+  <dict>
+    <key>Hour</key>
+    <integer>${RETRY_HOUR}</integer>
+    <key>Minute</key>
+    <integer>${RETRY_MIN}</integer>
+  </dict>
+  <key>EnvironmentVariables</key>
+  <dict>
+    <key>CLAUDE_AUTONOMOUS</key>
+    <string>1</string>
+    <key>CLAUDE_PROJECT_DIR</key>
+    <string>${PROJECT_DIR}</string>
+    <key>PATH</key>
+    <string>/usr/local/bin:/usr/bin:/bin:$HOME/.local/bin</string>
+  </dict>
+  <key>StandardOutPath</key>
+  <string>${LOG_FILE}</string>
+  <key>StandardErrorPath</key>
+  <string>${LOG_FILE}</string>
+</dict>
+</plist>
+PLIST
+
+      launchctl load "$PLIST_PATH" 2>/dev/null || true
+      log "Scheduled retry at ~${RETRY_TIME} via launchd ($PLIST_PATH)"
+      log "The plist auto-removes after running."
+      exit 0
+    fi
+
+    log "Rate limit detected (attempt $rate_limit_retries/$MAX_RATE_LIMIT_RETRIES)."
+    log "Sleeping ${RATE_LIMIT_WAIT}s until $(date -v+${RATE_LIMIT_WAIT}S '+%H:%M:%S' 2>/dev/null || date -d "+${RATE_LIMIT_WAIT} seconds" '+%H:%M:%S')..."
+    sleep "$RATE_LIMIT_WAIT"
+
+    # Check if plan still has tasks before retrying
+    if ! plan_has_tasks; then
+      log "All plan tasks completed during rate limit wait. Done."
+      break
+    fi
+    log "Retrying after rate limit..."
+    continue  # Retry same iteration
+  fi
+
+  # Reset rate limit counter on successful run
+  rate_limit_retries=0
+
   i=$((i + 1))
   if [ "$i" -le "$ITERATION_COUNT" ] && [ "$ITERATION_DELAY" -gt 0 ]; then
-    echo "Waiting ${ITERATION_DELAY}s before next iteration..." | tee -a "$LOG_FILE"
+    log "Waiting ${ITERATION_DELAY}s before next iteration..."
     sleep "$ITERATION_DELAY"
   fi
 done
 
-echo "=== Loop complete $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ===" | tee -a "$LOG_FILE"
+log "=== Loop complete $(date '+%Y-%m-%dT%H:%M:%S' 2>/dev/null || date) ==="