I can not reproduce this with latest VS Code out of source.
I can reproduce in vscode insiders. Thus it seems like I fixed the issue.
Let me know if you can repro out of source and I will reopen.

Potentially a candidate. Let me know if you think it is and I can search for the exact fix and port it to the release branch if we do a recovery release.

I don't think this is candidate worthy. Thanks for looking into it!

I can actually still reproduce this, though it seems racey.

1. Create a brand new folder
2. Create some hello.js in it, and open it.
3. Open the debug view
4. Reload the window
5. Run and Debug button is greyed out

https://memes.peet.io/img/20-04-d5946617-17ff-4281-b655-f006020b5ac3.webm

Pushed a potential fix. Can not really verify if it fixes since can not repro out of source.

This still repro's. I'll move this to next month and debug on my machine since it doesn't repro for you.

@connor4312 thanks for moving it. No need to debug on your machine since now I can reproduce it. But I can only reproduce it in the built version which makes debugging it a bit harder.

I got a fix for this though I couldn't actually verify it since I cannot repro out of source but it does happen in stable and insiders. I'll create a PR so you can try it out.

As mentioned in the PR I fully built VS Code from your changes and the issue is fixed.
Great fix and thanks for help @jeanp413