[Bug] Anthropic API Error: Internal Server Error (500) with no retry mechanism

Bug Description
Disappointed that I burned through much of my 5-hr quota on a task that--three times--ended with "API Error: 500 {"type":"error","error":{"type":"api_error","message":"Internal server
error"},"request_id":"req_011CYV8tSEUXz9jk1yfAyMdN"}" The error isn't actionable in any meaningful way, so it feels like a total waste

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.1.52
• Feedback ID: e3c1abac-1615-4972-bcc7-c4c6c0b23c71

Errors

[{"error":"Error: ENOENT: no such file or directory, open '/Library/Application Support/ClaudeCode/managed-settings.json'\n    at openSync (unknown)\n    at readSync (/$bunfs/root/claude:12:1441)\n    at F2 (/$bunfs/root/claude:6412:113)\n    at AO (/$bunfs/root/claude:6414:226)\n    at GP8 (/$bunfs/root/claude:6398:5806)\n    at s90 (/$bunfs/root/claude:6398:5579)\n    at <anonymous> (/$bunfs/root/claude:6398:4272)\n    at async a90 (/$bunfs/root/claude:6398:4654)\n    at async <anonymous> (/$bunfs/root/claude:11966:400)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:39:42.875Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CYV87fZetdJSPpppgQ5Yj\"}\n    at generate (/$bunfs/root/claude:267:28561)\n    at makeRequest (/$bunfs/root/claude:306:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:44:08.788Z"},{"error":"Error: File does not exist. Note: your current working directory is /Users/micahgiszack/Projects/InOrbit.\n    at call (/$bunfs/root/claude:1906:6346)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:46:20.015Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CYV8RKjo5izTQQza3GDUn\"}\n    at generate (/$bunfs/root/claude:267:28561)\n    at makeRequest (/$bunfs/root/claude:306:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:48:07.749Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CYV8esReaQR5WCckLWaFU\"}\n    at generate (/$bunfs/root/claude:267:28561)\n    at makeRequest (/$bunfs/root/claude:306:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:51:11.538Z"},{"error":"Error: EISDIR: illegal operation on a directory, read '/Users/micahgiszack/Projects/ProxyPilot'\n    at Zo_ (/$bunfs/root/claude:1760:243)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:52:02.642Z"},{"error":"Error: EISDIR: illegal operation on a directory, read '/Users/micahgiszack/Projects/ProxyPilot/ProxyPilotCLI/Sources'\n    at Zo_ (/$bunfs/root/claude:1760:243)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:52:29.108Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CYV8tSEUXz9jk1yfAyMdN\"}\n    at generate (/$bunfs/root/claude:267:28561)\n    at makeRequest (/$bunfs/root/claude:306:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-02-25T16:54:15.568Z"}]