The tracking client never talks directly to a device, it collects information locally, from the spooler, from the installed driver, and from the application that raised the print event. So an error that indicates "failed to connect to printer" is not coming from the tracking client. That you get a popup means we've collected the information we need to track the job, whether or not the job actually produces output, the client can't know, because it never talks to the device. We simply write the job to the database, if no output was generated, it would be up to the customer to delete that job using Job Manager.
If this behavior is consistent across multiple machines, that would tend to suggest the driver is the problem, but it sounds like a singular machine is available, so you may want to try addressing the driver as an expedient. If you aren't using the Universal driver, you might want to try that, generally we steer folks away from the Universal drivers, but to test that the problem lies with the driver...
On the Mac side, particularly if changing the driver on the Windows side seems to have an effect, you might want to try changing drivers, perhaps try the Apple-supplied driver, or any driver that supports the same printer control language used by the device. If you are using the Apple-supplied driver, you could try the one supplied by the manufacturer as well.
Beyond that, we would need to look at logs, and once the issue involves shipping logs, we'll have to move off the support forum, as there is no way for you to upload logs here, so a regular support case would need to be opened with us (Print Audit 6) or Ricoh (PCS Director) as appropriate.
Print Audit Support.