[Bug] Claude Code loses track of created plan files across session context

Bug Description
Claude Code loses track of the plan files it creates for itself even without compacting. I'm creating this in a new session because the transcript you include in feedback would be proprietary information. So another bug is the feedback tool needs to allow the user to select what can be included in the bug report.

Environment Info

• Platform: darwin
• Terminal: iTerm.app
• Version: 2.1.41
• Feedback ID: e0027c3c-a457-4f6f-b68c-fe897693e72d

Errors

[{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at ffD (/$bunfs/root/claude:187:1202)\n    at V9T (/$bunfs/root/claude:187:2080)","timestamp":"2026-02-13T03:06:49.281Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at I_ (/$bunfs/root/claude:186:10173)\n    at jn (/$bunfs/root/claude:187:2290)","timestamp":"2026-02-13T03:06:49.297Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at I_ (/$bunfs/root/claude:186:10173)\n    at jn (/$bunfs/root/claude:187:2290)","timestamp":"2026-02-13T03:06:49.300Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at ffD (/$bunfs/root/claude:187:1202)\n    at V9T (/$bunfs/root/claude:187:2080)","timestamp":"2026-02-13T03:06:49.303Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at zIA (/$bunfs/root/claude:2108:20850)\n    at k1B (/$bunfs/root/claude:2108:21755)\n    at <anonymous> (/$bunfs/root/claude:7549:510)","timestamp":"2026-02-13T03:06:49.304Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at I_ (/$bunfs/root/claude:186:10173)\n    at zVT (/$bunfs/root/claude:327:1160)","timestamp":"2026-02-13T03:06:49.305Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/remote-settings.json'\n    at openSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:947)\n    at O2 (/$bunfs/root/claude:11:50064)\n    at readSync (/$bunfs/root/claude:12:875)\n    at J2 (/$bunfs/root/claude:6149:113)\n    at h5 (/$bunfs/root/claude:6151:226)\n    at RBA (/$bunfs/root/claude:186:8273)\n    at r8R (/$bunfs/root/claude:186:8436)\n    at I_ (/$bunfs/root/claude:186:10173)\n    at FVT (/$bunfs/root/claude:327:1765)","timestamp":"2026-02-13T03:06:49.305Z"},{"error":"Error: ENOENT: no such file or directory, open '/Users/jkaster/.claude/re…

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