Hi @ChrisOsbakk,
See if any of these topics help:
https://forums.flightsimulator.com/t/logbook-showing-00-00-time-and-no-takeoffs-and-landings-still-an-issue-in-1-12-13-0/327325/150
https://forums.flightsimulator.com/t/flights-not-being-recorded-in-logbook/341161
https://forums.flightsimulator.com/t/logbook-not-working-stopped-90-hours-ago/344207
https://forums.flightsimulator.com/t/logbook-issues/345081
Or a search in Bugs for logbook:
Search results for ‘logbook category:200’ - Microsoft Flight Simulator Forums