[BUG] API Error (Request timed out.)

Environment

• Platform (select one):
• [X] Anthropic API
• [ ] AWS Bedrock
• [ ] Google Vertex AI
• [ ] Other: <!-- specify -->
• Claude CLI version: 1.0.53 (Claude Code)
• Operating System: WSL1 (Linux DE1-WW-004 4.4.0-22621-Microsoft #5415-Microsoft Fri Jan 01 08:00:00 PST 2016 x86_64 GNU/Linux)
• Terminal: Alacritty

Bug Description

API Error (Request timed out.) happens regularly, but mostly during todo updates for some reason.

Steps to Reproduce

1. Run any long-standing agentic task.
2. The task fails with an almost 100% rate with API errors.

Expected Behavior

No API Errors

Actual Behavior

API Error (Request timed out.) or API Error (Connection error.) with 10 unsuccessful retries until total failure.

Additional Context

<img width="709" height="316" alt="Image" src="https://github.com/user-attachments/assets/b2d41613-bea2-4fcf-a061-223027277e7e" />