[Bug] Context window limit reached consistently at ~84% of session usage

Bug Description
I'm hitting the limit EVERY SINGLE TIME at 84% of session. This is not a good experience. Feel like I'm paying for a half baked feature

Environment Info

• Platform: darwin
• Terminal: iTerm.app
• Version: 2.1.25
• Feedback ID: 05aada8b-4cde-4e25-a04d-fe083f770ab7

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 (/$bunfs/root/claude:4793:4342)","timestamp":"2026-01-30T16:42:57.776Z"},{"error":"AbortError: The operation was aborted.\n    at unknown\n    at abortChildProcess (node:child_process:935:42)\n    at onAbortListener2 (node:child_process:35:24)\n    at abort (unknown)\n    at <anonymous> (/$bunfs/root/claude:3000:209)","timestamp":"2026-01-30T16:43:00.585Z"},{"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> (/$bunfs/root/claude:5149:2153)","timestamp":"2026-01-30T17:19:13.656Z"},{"error":"Error: ENOENT: no such file or directory, scandir '/Library/Application Support/ClaudeCode/.claude/skills'\n    at readdirSync (unknown)\n    at <anonymous> (/$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":"2026-01-30T17:20:29.051Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/claude:162:3940)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T17:23:24.035Z"},{"error":"Error: Request was aborted.\n    at FIR (/$bunfs/root/claude:1688:44936)\n    at A90 (/$bunfs/root/claude:5062:7413)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T17:23:41.090Z"},{"error":"Error: Request was aborted.\n    at makeRequest (/$bunfs/root/claude:162:3940)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T17:37:20.426Z"},{"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 (/$bunfs/root/claude:4793:4342)","timestamp":"2026-01-30T17:39:58.878Z"},{"error":"Error: 429 {\"type\":\"error\",\"error\":{\"type\":\"rate_limit_error\",\"message\":\"This request would exceed your account's rate limit. Please try again later.\"},\"request_id\":\"req_011CXdzYj45RSrvFbmX96foF\"}\n    at generate (/$bunfs/root/claude:145:37865)\n    at makeRequest (/$bunfs/root/claude:162:5435)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-01-30T17:55:47.058Z"}]