@CalebJohn, these issues are most likely due to this change: Desktop: Stop watching external edits by CalebJohn · Pull Request #1981 · laurent22/joplin · GitHub I see this as well, Joplin starts watching the file then stop right away, and in my case I know that's because the process that starts is different from the one that opens the file (it goes through a wrapper). So the onClose event is fired immediately and Joplin stops watching the file.
That makes me think we can't reliably know if a file is closed or not, so we might have to undo this particular change.