PDF Compaction Fails with Anthropic API "Conversation Too Long" Error

Bug Description
/compact fails with "Conversation too long" error after reading PDF. Full details in claude-code-compact-bug-report.md and session-context.md. Test
PDF available at https://www.nikhef.nl/~mjg/Antares/DAQ/doc/pjl-thesis.pdf

Environment Info

• Platform: darwin
• Terminal: iTerm.app
• Version: 1.0.60
• Feedback ID: f12c51f6-b0eb-45ba-9e43-f634197a27f6

Errors

[{"error":"Error: Command failed: security find-generic-password -a $USER -w -s \"Claude Code\"\nsecurity: SecKeychainSearchCopyNext: The specified item could not be found in the keychain.\n\n    at genericNodeError (node:internal/errors:983:15)\n    at wrappedFn (node:internal/errors:537:14)\n    at checkExecSyncError (node:child_process:924:11)\n    at execSync (node:child_process:996:15)\n    at i7 (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:865:5196)\n    at file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:777:49014\n    at Q (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:674:14420)\n    at kJ (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:777:46725)\n    at XH (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:777:45592)\n    at I9 (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:777:51640)","timestamp":"2025-07-25T02:04:01.869Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at BX (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:1184)\n    at file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:912\n    at Array.map (<anonymous>)\n    at QX (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:903)\n    at g_B (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2525:7705)\n    at gM (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:19859)\n    at gv (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:42847)\n    at fv (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38368)\n    at RS (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38296)\n    at ZR (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38150)","timestamp":"2025-07-25T02:09:43.063Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at BX (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:1184)\n    at file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:912\n    at Array.map (<anonymous>)\n    at QX (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1491:903)\n    at g_B (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:2525:7705)\n    at gM (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:19859)\n    at gv (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:42847)\n    at fv (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38368)\n    at RS (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38296)\n    at ZR (file:///Users/anders/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38150)","timestamp":"2025-07-25T02:11:54.137Z"}]