[Bug] Auto-Compact Fails and Requires Application Restart

Bug Description
Even when i am not getting the low context % at the bottom ,if i try to compact i get the a message that i need to go back a few messages and try to comapct again, this never works btw. What i need to every time is i have to exit claude code and then start it again, resume my conversation and then i can compact.

Environment Info

• Platform: win32
• Terminal: vscode
• Version: 2.0.14
• Feedback ID: dc95ae8b-84e6-49d2-b006-a59230bd961c

Errors

[{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at hK (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:729)\n    at file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:457\n    at Array.map (<anonymous>)\n    at tF (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:448)\n    at OlB (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:12745)\n    at G$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:73:19415)\n    at ka (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:42814)\n    at S9 (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38355)\n    at Wm (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38283)\n    at z$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38137)","timestamp":"2025-10-14T04:34:50.886Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at hK (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:729)\n    at file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:457\n    at Array.map (<anonymous>)\n    at tF (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:448)\n    at OlB (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:12745)\n    at G$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:73:19415)\n    at ka (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:42814)\n    at S9 (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38355)\n    at Wm (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38283)\n    at z$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38137)","timestamp":"2025-10-14T04:34:51.083Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at hK (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:729)\n    at file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:457\n    at Array.map (<anonymous>)\n    at tF (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:448)\n    at OlB (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:12745)\n    at G$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:73:19415)\n    at ka (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:42814)\n    at S9 (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38355)\n    at Wm (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38283)\n    at z$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38137)","timestamp":"2025-10-14T04:34:51.085Z"},{"error":"Error: Language not supported while highlighting code, falling back to markdown: \n    at hK (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:729)\n    at file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:457\n    at Array.map (<anonymous>)\n    at tF (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:448)\n    at OlB (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:2123:12745)\n    at G$ (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:73:19415)\n    at ka (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:42814)\n    at S9 (file:///C:/Users/Bain/AppData/Roaming/npm/node_modules/@anthropic-ai/claude-code/cli.js:75:38355)\n    at Wm (file:///C:/Users/

Note: Error logs were truncated.