You may find yourself… supporting developers working behind a corporate non-transparent HTTP web proxy which is implemented in some environments and not others. And you may ask yourself, “How do I work this?” - with a nod to the Talking Heads, whose “Once in a Lifetime” seems strangely appropriate when dealing with proxy configurations which work sometimes but not others. In Windows, a host of CLI tools commonly used in development don’t inherit Windows proxy settings.

Azure VPN Gateway’s SSTP Point-to-Site (P2S) connections to private VNETs can cause networking issues in WSL. Symptoms include hanging SSL connections, frozen database clients, and DB clients failing in Docker/Kubernetes networks. I encountered this with a SSL secured MySQL connection which would just hang with nothing informative. Worked fine from the Windows host. The culprit: MTU mismatches. The Problem MTU (Maximum Transmission Unit) is the largest packet size that can be transmitted over a network connection.