Printing job stuck pending but a restart of Print connecter service gets them printed

Brandon_Emlinger Thanks for that info, that (1.83.8291) version is the latest one so far. 

For folks hitting this, and where restart of the Print Connector service is helping re-establish the connection with UP or get print jobs working again, I can suggest couple of items. 

1. We recently added a sample PowerShell script that helps reset just the individual printer. You can download this on the Connector host machine, (edit it to uncomment the invoke method at the very end), and run it from an elevated PS window. It just takes in the printer name (matching the printer name locally on that Connector machine). There's no service restart involved here, and the impacted is limited to just one printer. 

This isn't fixing the root cause (we don't know the issue yet), but is a better alternative than performing a restart on the Print Connector service and potentially impacting other printers/users.

2. For finding the root cause, I would suggest reaching out to our Azure Support and filing a support case - https://aka.ms/upsupport-azureportal

Our support team can guide you in collecting the required information. Hopefully once the issue is identified, you won't have to reset the printer (or the service).