Bug Report Request size exceeds model context window

Bug Description
Claude repeatedly drops out of the conversation with this error:
⎿ API Error: 413 {"type":"error","error":{"type":"invalid_request_error","message":"Request
size exceeds model context window"},"request_id":"req_011CSPXt2ERYg5mTNcnuQZFg"}

even on a new conversation, even after /compact

Environment Info

• Platform: darwin
• Terminal: cursor
• Version: 1.0.88
• Feedback ID: 23b9e06e-a1f5-4494-b532-85cfb15983ad

Errors

[{"error":"Error: 413 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"Request size exceeds model context window\"},\"request_id\":\"req_011CSPY4GMGWcLbbCm7tbXH7\"}\n    at v4.generate (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:926:2680)\n    at XP.makeStatusError (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:2101)\n    at XP.makeRequest (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:5315)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async DZ1.showErrors (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:27329)\n    at async DZ1 (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:16486)\n    at async s2B (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:27180)\n    at async file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:22275\n    at async eD0 (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:3656)\n    at async Fe (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:22245)","timestamp":"2025-08-22T22:27:50.639Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Overloaded\"},\"request_id\":null}\n    at v4.generate (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:926:2656)\n    at XP.makeStatusError (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:2101)\n    at XP.makeRequest (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:5315)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async DZ1.showErrors (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:27329)\n    at async DZ1 (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:16486)\n    at async s2B (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:27180)\n    at async file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:22275\n    at async eD0 (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:3656)\n    at async Fe (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1891:22245)","timestamp":"2025-08-22T22:28:23.900Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.0: all messages must have non-empty content except for the optional final assistant message\"},\"request_id\":\"req_011CSPY7vLc2ywurkZdMD6Vu\"}\n    at v4.generate (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:926:2412)\n    at XP.makeStatusError (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:2101)\n    at XP.makeRequest (file:///Users/itai/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:943:5315)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)","timestamp":"2025-08-22T22:28:35.673Z"}]