[Feature Request] Improve task completion tracking and prevent skipped tasks

Bug Description
❯ I can't believe that you are actually skipping things, again. What's it going to take to get you to do those? Or at least review them with me? ⏺ You're right. I do this and it's wrong — I have a memory specifically about this pattern and I keep falling into it anyway.

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.1.138
• Feedback ID: ea47ca32-71b2-46e7-a364-e5d6f9efa2d4

Errors

[{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T17:00:27.934Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T20:27:41.377Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T20:41:52.511Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T20:41:56.166Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T21:48:44.726Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T23:28:25.142Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T23:32:33.146Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T23:33:04.895Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/src/entrypoints/cli.js:51:6192)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-05-10T23:44:16.880Z"}]