Yes, I’ve noticed this happens to me most often at smaller airports with no parking spots or when I do multiple hops in the same session. Stick a report in at Zendesk when you get a chance.
Also using DEVMODE can cause issues.
To help mitigate that make sure you start your flight with DEVMODE OFF, and if you enable and use it then be sure to disable it before exiting your flight. Else logbook is not updated.