Hey, thanks for the report. This is a known issue with image generation after the 2.4 release. A few users have started seeing “Connection stalled” errors and silent failures.
Good news: it’s not related to your Legacy Pro plan. The bug affects all users, no matter what subscription they’re on.
The team is aware, but there’s no workaround yet. We’ll post updates here: Image Generation Connection Error in Cursor 2.4
About the “silent failure instead of a normal error” part, I agree it’s annoying. Ideally it should show a clear error instead of just hanging.