I encountered some issues running WebStorm and I think I finally solved them. This was an annoying bug that was a mix of WebStorm and OSX behavior that I didn’t ask for. TODO: Pinentry Image This is the prompt that you get on OSX running Pinentry. I was getting this randomly all throughout the day just running JetBrains products. That’s really annoying. You can see that WebStorm is trying to run git-upload-pack when I get the Pinentry prompt, and that is what triggered it.