I have a print server running Windows Server 2012 which is shared in a domain and is used by terminal services clients.
The domain network spans between countries using tunnels and in some situations the print server and the printers are not in the same physical network and in this situations when the network is busy big documents fail to print.
If I check the Print Queue Window I don't get very much data on what happens the only available fields displayed are Document Name
Status
Owner
Pages
Size
Submitted
Port
Sometimes Size is empty and Status doesn't give too much information. The only solution remaining is to select Cancel All Documents
from that same Print Queue window and when some print job is stuck that usually doesn't work.
Is there a way for system administrators to better track and debug what happens with files stuck in the print spooler ?
Since you mentioned tunnels and remote printers, I would first use Wireshark to collect network data related to the print jobs and try to simulate the behavior (i.e. failure printing big files). You might be able to identify a connection being closed by either side.
Failing that, using Process Monitor to capture low-level syscall usage data for the Print Spooler might help you identify if the problem is local to the print server.
You can also follow the steps explained in the Print Spooler Crash Troubleshooting Steps TechNet post.