[BUG] Claude Code CLI and MAC App (Code & Cowork) Request Timeout

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

• macOS 26.2, M4, direct connection (no VPN/proxy)
• curl --http1.1 https://api.anthropic.com ✅ works
• curl https://api.anthropic.com ❌ times out (HTTP/2)
• Claude Code fails with UNKNOWN_CERTIFICATE_VERIFICATION_ERROR (misleading error)
• Claude Code CLI and Mac Desktop App (Code Tab) all requests timeout.

What Should Happen?

curl https://api.anthropic.com with (HTTP/2) ✅ works

Error Messages/Logs

CLI: Claude Code fails with UNKNOWN_CERTIFICATE_VERIFICATION_ERROR (misleading error) or API Error: Unable to connect to API (UNKNOWN_CERTIFICATE_VERIFICATION_ERROR).

Mac App (Code): Could not load connectors directory or session failed ...

Mac App (Cowork): Failed to start Claude's workspace
Can't reach the Claude API from Claude's workspace.
Restarting Claude or reconnecting to your network sometimes resolves this.

Steps to Reproduce

1. Active Claude Code CLI in a folder
2. Run claude
3. Ask a question
4. Claude trys to connect 10 times all connects time out

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.37 (Claude Code)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

It started about 2 days ago