[Bug] Conversation Compact Functionality Regression in Context Management

Bug Description
I have to rewind to about 25%+ context remaining in order to compact conversation unless I let it run into auto-compact. I used to be able to compact as low as 0% remaining.

Windows 11 Pro (version 24H2)
Processor: AMD Ryzen 7 7800X3D 8-Core Processor (4.20 GHz)
Installed RAM 64.0 GB (63.2 GB usable)
System type 64-bit operating system, x64-based processor

Claude Code session was within VSCode version 1.104.2

Environment Info

• Platform: win32
• Terminal: vscode
• Version: 2.0.9
• Feedback ID: ce9e0476-739a-41f2-b82d-1f76b02a08da

Errors

[{"error":"Error: Tool MultiEdit not found\n    at q2B (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:7881)\n    at NC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:19415)\n    at Cp (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:42814)\n    at Z9 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38355)\n    at Eh (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38283)\n    at kC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38137)\n    at jH (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:35216)\n    at P6 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:4841)\n    at B5 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:32461)\n    at nY (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:24920)","timestamp":"2025-10-06T23:08:28.735Z"},{"error":"Error: Tool MultiEdit not found\n    at q2B (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:7881)\n    at NC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:19415)\n    at Cp (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:42814)\n    at Z9 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38355)\n    at Eh (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38283)\n    at kC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38137)\n    at jH (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:35216)\n    at P6 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:4841)\n    at B5 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:32461)\n    at nY (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:24920)","timestamp":"2025-10-06T23:08:28.788Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at VK (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:1218)\n    at file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:2206\n    at Array.map (<anonymous>)\n    at VK (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:2177)\n    at file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:2093\n    at Array.map (<anonymous>)\n    at VK (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:2082)\n    at file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:946\n    at Array.map (<anonymous>)\n    at hX (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:937)","timestamp":"2025-10-06T23:08:28.872Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at VK (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:1218)\n    at file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:946\n    at Array.map (<anonymous>)\n    at hX (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:937)\n    at E2B (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2204:12993)\n    at NC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:32:19415)\n    at Cp (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:42814)\n    at Z9 (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38355)\n    at Eh (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38283)\n    at kC (file:///C:/Users/blake/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:34:38137)","timestamp":"2025-10-06T23:08:28.

Note: Error logs were truncated.