We are very close to getting Microsoft UP to work but have run into an issue where if multiple print jobs are being sent to the server queue, it will only display one job at a time. It’s not until the job is canceled that the next chronological print job is displayed.
An example scenario:
2 print jobs are sent to the printer: Document1 and Document2
On the PC, both print jobs are seen.
On the server, only the first one shows up
The second one shows after canceling the first one
@Darren-C currently the connector does send print jobs to the local printer queue of the host machine one at a time, part of the thinking is that if the printer is offline, wouldn't it be better to queue the print job in the cloud service instead of the local spooler (which is subject to power outages, etc.). In your scenario, it seems that the printer queue puts each job on hold ('pause') state. For now I'll assume it is to enable some form of print job release mechanism.
If the printer queue does not put jobs on 'pause' and returns success, the connector will process the next job. For example, if the physical printer has a hard drive itself to hold print jobs and when connector sends the job to the printer queue, the printer driver sends the job to the physical printer and the printer holds the job within its hard drive and returns success, then the printer queue will reflect a successful print and the connector will move to the next job.