There’re several different reasons when local printer is not available at Terminal Services Session, below are my check list, hope it helps.
#1. Printer redirection is disabled at Terminal Server
First thing to check is whether the server has disabled the printer redirection.
Also ensure it enable the use of user settings.
Path: Control Panel > Administrative tools > Terminal Services Configuration
Check group policy
Path: Start > Run > gpedit.msc > Local Computer Policy > Computer Configuration > Administrative Templates > Windows Components > Terminal Services > Client/Server data redirection
Ensure the printer redirection is not disabled.
Reference:
http://social.technet.microsoft.com/Forums/en/winserverTS/thread/619d78a1-dc47-45cf-a078-e9fba492dd1f
http://social.technet.microsoft.com/Forums/en/winserverTS/thread/4ebf9a34-85f3-4b91-9750-48124b9885ba
#2. Local resources (Printer) is not checked in the RDP connection settings
Ensure the “Printers” checkbox is checked under the “Local devices and resources” group.
#3. Printer driver is not available at Terminal Server
In certain cases, the issue was caused by printer driver is not available at the server, you might want to install it there.
Reference: http://technet.microsoft.com/en-us/library/cc758836(WS.10).aspx
#4. Printer is not using COM, LPT, or USB port
Refer to more details at http://support.microsoft.com/kb/302361.