[Bug] Compaction fails with "Conversation too long" error when context limit reached

Bug Description
When an agent is performing a long-running task, it often reaches the Context limit reached · /compact or /clear to continue.

however if I type /compact to continue the large task I get this message:

Error: Error during compaction: Error: Conversation too long. Press esc twice to go up a few
messages and try again.

this is extremely frustrating and I have to copy the execution plan to a new session to continue. the context limit should be reached with enough context to compact

Environment Info

• Platform: darwin
• Terminal: ghostty
• Version: 2.1.25
• Feedback ID: 021d3ea4-a797-495d-a489-c1ae67caf78b

Errors

[{"error":"Error: ENOENT: no such file or directory, scandir '/Library/Application Support/ClaudeCode/.claude/skills'\n    at readdirSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:2063)\n    at iW (/$bunfs/root/claude:11:35715)\n    at readdirSync (/$bunfs/root/claude:12:2024)\n    at wQR (/$bunfs/root/claude:1783:380)\n    at wQR (/$bunfs/root/claude:1783:1350)\n    at <anonymous> (/$bunfs/root/claude:1783:4670)\n    at <anonymous> (/$bunfs/root/claude:1783:5401)\n    at A (/$bunfs/root/claude:11:7259)\n    at Ay8 (/$bunfs/root/claude:4793:4342)","timestamp":"2026-01-30T13:47:26.073Z"},{"error":"Error: NON-FATAL: Lock acquisition failed for /Users/aferraro/.local/share/claude/versions/2.1.25 (expected in multi-process scenarios)\n    at kzR (/$bunfs/root/claude:3940:2098)\n    at JxA (/$bunfs/root/claude:3940:1209)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T13:47:26.090Z"},{"error":"AbortError: The operation was aborted.\n    at unknown\n    at abortChildProcess (node:child_process:935:42)\n    at onAbortListener2 (node:child_process:35:24)\n    at abort (unknown)\n    at <anonymous> (/$bunfs/root/claude:5149:2153)","timestamp":"2026-01-30T13:59:51.691Z"},{"error":"Error: ENOENT: no such file or directory, scandir '/Library/Application Support/ClaudeCode/.claude/skills'\n    at readdirSync (unknown)\n    at <anonymous> (/$bunfs/root/claude:12:2063)\n    at iW (/$bunfs/root/claude:11:35715)\n    at readdirSync (/$bunfs/root/claude:12:2024)\n    at wQR (/$bunfs/root/claude:1783:380)\n    at wQR (/$bunfs/root/claude:1783:1350)\n    at <anonymous> (/$bunfs/root/claude:1783:4670)\n    at <anonymous> (/$bunfs/root/claude:1783:5401)\n    at A (/$bunfs/root/claude:11:7259)\n    at Ay8 (/$bunfs/root/claude:4793:4342)","timestamp":"2026-01-30T14:01:04.420Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 212427 tokens > 200000 maximum\"},\"request_id\":\"req_011CXdiEfgZMQYCFc81EaAHa\"}\n    at generate (/$bunfs/root/claude:145:37655)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T14:21:53.919Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 213458 tokens > 200000 maximum\"},\"request_id\":\"req_011CXdiF3ZCqkmxFeat45gJc\"}\n    at generate (/$bunfs/root/claude:145:37655)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T14:21:57.893Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 214789 tokens > 200000 maximum\"},\"request_id\":\"req_011CXdiFAGmXEsFQ8HxjPU9b\"}\n    at generate (/$bunfs/root/claude:145:37655)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T14:21:59.392Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 216259 tokens > 200000 maximum\"},\"request_id\":\"req_011CXdiFEv59AwS7cnxNNoGB\"}\n    at generate (/$bunfs/root/claude:145:37655)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T14:22:00.738Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"prompt is too long: 217673 tokens > 200000 maximum\"},\"request_id\":\"req_011CXdiFb33VV1KJ28P9EZGh\"}\n    at generate (/$bunfs/root/claude:145:37655)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T14:22:05.529Z"},{"error":"Error: Conversation too long. Press esc twice to go up a few messages and try again.\n    at bhT (…

Note: Content was truncated.