Printing on network and local printers over VPN connections and RDP connections can be somewhat tricky if not configured properly.  Use the following steps to aid you in correcting the inability to connect to these local and network printers if issues are occuring.  

First - Verify that you have the same exact printer driver installed on both servers or workstations involved.  This can be verified by opening the "Server properties" window of the printers and devices area.  On the "Drivers" tab, you will see all drivers that are installed for printers.

Second - On the workstation you are trying to connect printers to, you will need to edit the registry in order to allow connections to printing ports over RDP. (Use steps below)

- Open regedit (Start, Run, Regedit)

- Expand HKCU\Software\Microsoft\Terminal Server Client\Default\AddIns\RDPDR 

- Add a DWORD value with the name of FilterQueueType

- Modify the data to FFFFFFFF (eight "f"s)

- Reboot the workstation

Third - On the "Options" button of your RDP connection, you will see a "Local Resources" tab.  Be sure that "Printers" are checked in the resources you want to use when connected.

Fourth - Connect your VPN / RDP or both and login and verify that the printers you are trying to connect to are listed on the remote machine and are able to print.

This will allow the printers to connect across the VPN/RDP connections.