macOS SSH Proxy Hang Issue Analysis | Generated by AI
Good references! Here’s how they relate to your SSH proxy hang issue:
Reference Analysis
Reference 1 (Apple Discussions) - Partially relevant
- Similar symptoms: SSH hangs with no error, tcpdump shows no traffic
- Different root cause: Cloudflare Warp VPN blocking SSH, not HTTP proxy env vars
- Takeaway: VPN/proxy software can silently block SSH in multiple ways
Reference 2 (The Register - Catalina SSH bug) - Highly relevant ✅
- Direct match: macOS SSH + proxy configuration causing hangs
- Root cause: Auto Proxy Discovery interfering with SSH
- Key insight: The bug affected SSH to ports >8192 using hostnames, and disabling proxy settings fixed it
How They Support Your Answer
Your diagnosis (HTTP_PROXY/HTTPS_PROXY env vars intercepting SSH) is spot-on. Reference 2 confirms that macOS SSH + proxy settings = known hang issue. The Catalina bug was specifically about Auto Proxy Discovery, but the pattern is identical:
- Proxy configuration active
- SSH attempts connection
- Proxy intercepts/mishandles the connection
- SSH hangs silently
Suggested Addition to Your Answer
You could add this context at the end:
---
## Known macOS SSH + Proxy Issues
This is a recurring pattern on macOS:
- **macOS 10.15.4 bug**: Auto Proxy Discovery broke SSH to ports >8192 ([source](https://www.theregister.com/2020/04/01/apples_macos_catalina_ssh/))
- **VPN interference**: Apps like Cloudflare Warp can silently block SSH ([source](https://discussions.apple.com/thread/255263733))
- **HTTP_PROXY env vars**: Clash/V2Ray proxies intercept all TCP including SSH to LAN IPs (this case)
The common thread: proxy/VPN software treating SSH as HTTP traffic and failing to route it correctly.
Both references validate that your diagnosis is part of a well-documented class of macOS SSH issues related to proxy/VPN interference.