Compact Operation Fails to Trigger Automatically and Manual Execution Incomplete

Bug Description
Compact not running automatically and not completing successful when done manually

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 1.0.45
• Feedback ID: 434ad04e-ed06-4064-84fb-3b24bcef51b4

Errors

[{"error":"Error: Command failed: security find-generic-password -a $USER -w -s \"Claude Code\"\nsecurity: SecKeychainSearchCopyNext: The specified item could not be found in the keychain.\n\n    at genericNodeError (node:internal/errors:983:15)\n    at wrappedFn (node:internal/errors:537:14)\n    at checkExecSyncError (node:child_process:882:11)\n    at execSync (node:child_process:954:15)\n    at qD (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:702:3921)\n    at file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:9350\n    at Q (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:526:14406)\n    at mC (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:8496)\n    at uC (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:7361)\n    at zB (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:11970)","timestamp":"2025-07-10T01:11:51.131Z"},{"error":"MaxFileReadTokenExceededError: File content (42386 tokens) exceeds maximum allowed tokens (25000). Please use offset and limit parameters to read specific portions of the file, or use the GrepTool to search for specific content.\n    at vU6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1416:432)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async Object.call (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1411:5788)\n    at async g$6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:11720)\n    at async Oz1 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:8441)\n    at async wc (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1901:774)\n    at async b$6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:7586)\n    at async x$6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:7071)\n    at async zE (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:5532)\n    at async NQA (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2521:544)","timestamp":"2025-07-10T01:14:07.392Z"},{"error":"Error: Agent 1: Last message was not an assistant message\n    at NQA (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2524:62)\n    at async Object.call (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2526:791)\n    at async g$6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:11720)\n    at async Oz1 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:8441)","timestamp":"2025-07-10T02:32:33.414Z"},{"error":"Error: Agent 1: Last message was not an assistant message\n    at NQA (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2524:62)\n    at async Object.call (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2526:791)\n    at async g$6 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:11720)\n    at async Oz1 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1921:8441)","timestamp":"2025-07-10T02:54:32.046Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 211755 tokens > 200000 maximum\"}}\n    at D6.generate (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1305:12578)\n    at pq.makeStatusError (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1322:2100)\n    at pq.makeRequest (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1322:5311)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async VO2.mA1.showErrors (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1691:23185)\n    at async mA1 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1691:12720)\n    at async VO2 (file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1691:23034)\n    at async file:///Users/johnmerriman/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1691:18138\n    at async N0A (file:///Users/john

Note: Error logs were truncated.