[Bug] Session compaction loses context priority and critical blockers

[matssun]

Bug Description comapction do not work as expected: So you lost track because of your compaction. The compaction algorithm does not work accordingly.

⏺ You're absolutely correct. The session compaction/summary failed to properly preserve the priority and urgency of where we were in the conversation.

What the summary should have emphasized:

CRITICAL BLOCKER - ACTIVE INVESTIGATION:

• 78 files have broken imports: from monitoring_infrastructure import StructuredLogger
• Component was deleted but files never migrated
• User questioning architecture: should components have Sidecar?
• RESUME: Investigating what replaced StructuredLogger and how to fix the 78 files

Original Task (BLOCKED by above):

• Regenerate IntelliCode database
• Test BUILD.bazel generation

What the summary actually said:

• Listed tasks chronologically
• Mentioned the 78 files as a "discovery"
• Didn't clearly mark it as THE BLOCKER that stopped progress

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.0.64
• Feedback ID: bd02dcf9-c527-440c-b147-177fdc010b4e

Errors

[{"error":"Error: Request was aborted.\n    at _createMessage (/$bunfs/root/claude:128:3151)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-12-10T23:15:51.546Z"},{"error":"Error: Shell df89f5 is not running, so cannot be killed (status: completed)\n    at call (/$bunfs/root/claude:2717:1839)\n    at async RtD (/$bunfs/root/claude:2904:16747)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-12-11T11:30:45.103Z"},{"error":"Error: Shell 10716e is not running, so cannot be killed (status: failed)\n    at call (/$bunfs/root/claude:2717:1839)\n    at async RtD (/$bunfs/root/claude:2904:16747)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-12-11T11:30:45.113Z"},{"error":"Error: Shell 095fb9 is not running, so cannot be killed (status: failed)\n    at call (/$bunfs/root/claude:2717:1839)\n    at async RtD (/$bunfs/root/claude:2904:16747)\n    at processTicksAndRejections (native:7:39)","timestamp":"2025-12-11T11:30:45.113Z"},{"error":"Error: ENOENT: no such file or directory, posix_spawn '/opt/homebrew/Caskroom/claude-code/2.0.64/claude'\n    at spawn (unknown)\n    at spawn (node:child_process:667:35)\n    at spawn (node:child_process:14:39)\n    at execFile (node:child_process:59:20)\n    at PqA (/$bunfs/root/claude:29:5926)\n    at <anonymous> (/$bunfs/root/claude:31:169)\n    at new Promise (native:1:11)\n    at Nw (/$bunfs/root/claude:29:6132)\n    at Nw (/$bunfs/root/claude:29:6225)\n    at call (/$bunfs/root/claude:2034:1180)","timestamp":"2025-12-11T12:10:15.962Z"},{"error":"Error: ENOENT: no such file or directory, posix_spawn '/opt/homebrew/Caskroom/claude-code/2.0.64/claude'\n    at spawn (unknown)\n    at spawn (node:child_process:667:35)\n    at spawn (node:child_process:14:39)\n    at execFile (node:child_process:59:20)\n    at PqA (/$bunfs/root/claude:29:5926)\n    at <anonymous> (/$bunfs/root/claude:31:169)\n    at new Promise (native:1:11)\n    at Nw (/$bunfs/root/claude:29:6132)\n    at Nw (/$bunfs/root/claude:29:6225)\n    at EzB (/$bunfs/root/claude:4293:17615)","timestamp":"2025-12-11T12:12:48.994Z"}]