I thought I would post this in order to help anyone that encounter this situation. There are many factors that can cause a printing issue, so I am going to outline the setup: Parallels Desktop v3.0 Using Parallel Port Option Using USB Connected Printer Printer does not appear in Windows Explorer -OR: "Win32 error code returned by the print processor: 2." in Event Log Try the following: Configure the virtual machine to Autoconnect USB to the Guest OS After this, if the printer is not appearing in Windows Explorer (Start->Settings->Printers), reinstall Parallel Tools If the printer is appearing, but you cannot print and get the message listed above in the Event Log, open up Device Manager. Check to see if there is an exclaimation by the LPT1 listing. If it is, go to properties for the item. You may see a message stating the drivers are not installed for the device. If this is the case, click the Update Driver button. Select search for recommended driver option and make sure the Windows Update checkbox is selected for places to look for drivers. After Windows contacts Windows Update, it should find that MSPORTS is the best suited driver. Once installed, the Device Manager will be updated. You should now be able to print, if the specific conditions listed above affect you. Hope this information helps someone out.