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Why do all requests fail with gateway timeout

At a glance
Goal: Fix gateway timeout on first run
Time: 2 minutes
Plugins: None
Prerequisites: Set up Dev Proxy

If you're running the proxy for the first time, it can happen that the network access configuration didn't propagate timely and the proxy started without access to your network.

Close the proxy by pressing Ctrl + C in proxy's window and restart the proxy and it should be working as intended.

See also