This has been fixed in the Windows 10 KB5001567 update.
The week of March 10th, Windows started rolling out a couple software updates (KB5000802 and KB5000808). Check-ins users that have not switched to Universal Printing will run into issues with printing after these latest updates.
How do I know if Universal Printing is enabled or not?
If you see the Labels tab on the top bar in Check-ins, you are good to go!
If you aren't seeing that tab, head over to the Stations Tab. Select the gear icon on the top right and choose Universal Printing.
Eventually, we will be transitioning everyone over to Universal Printing so if you are running into this issue with the latest Windows updates, now would be a great time to make the switch!
However, if you are unable to switch to Universal Printing because you are using different labels in your Dymo Twin Turbo printer, you can rollback the latest Windows 10 Updates and continue to use Legacy printing until we release an update for Universal Printing that supports this feature.