The user had recently uninstalled and re-installed the printer driver for their HP OfficeJet Pro 8500 A910g, which was plugged into their local workstation.
I shared the printer on their network again, re-installed the driver to their server from the network share, restarted their RemoteApp for Tracker, and still was unable to print to this printer.
Print job made it to printer without issue, but just hung-up, with a status of 'Printing'. It would eventually error out.
Print queue for this printer showing from the server had a status of "Printer: User Intervention".
Restarting the printer spooler on either machine did not resolve the issue, nor did printing directly to the printer/bypassing print spooling.
Researched the issue online, found a link stating that this a known issue with HP printers where if the ink cartridges had been replaced with an off-brand cartridge, it would not allow it to print. (Link to article listed below)
http://h30434.www3.hp.com/t5/Printing-Issues-Troubleshooting/HP-Officejet-Pro-8500-A910g-printing-but-never-does/td-p/1181657