I've seen this recently, but only in the last few months, after years of using Little Snitch with Spaces, so I think it's a new thing either with the most recent version of Little Snitch, or macOS Ventura.

Same experience. Worked perfectly fine before.

I wrote w LS support, it is a Ventura-related issue. They've made a request, but it appears Apple has yet to address the problem.

This, unfortunately, is a major problem for my use of LS. Interrupted connection attempts happen silently and result in different behavior for each app they affect.

I've had the most problems with requests from pycharm, where the binary is updated regularly and needs a bunch of re-authorizations.

I'm ready to give up on Spaces, it is so poorly supported by Apple at this point.

I think so? If that's what the thing is called when I swipe between desktops. I've only used LuLu on this machine though, and it seems to have no problem (though I guess I wouldn't notice if it wasn't popping up sometimes).

One thing I have noticed with LuLu is that the connection attempt sometimes shows the address of my VPN server rather than the actual upstream destination address of the request. But sometimes it shows the upstream - I'm not sure what the pattern is there.

Yup. They have an FAQ on the subject, and claim it's a Ventura bug and not one of theirs.

I've filed a bug report with Apple, for all the good that will do.

What's weird, annoying, and frustrating is that it will work correctly for the first day or two after a reboot, then start exhibiting the bad behavior. Once the "wrong desktop" popups start, they continue until the next reboot.