If you’re having trouble copying & pasting files to/from TS sessions it’s probably because you didn’t turn on the “Disk Drives” option of the RDP session.

Using the TS Copy / Paste / drive mapping option is also a good alternative for securely transmitting data to/from a customer site because the data will be encrypted as part of the RDP data stream.

Note that the drive mapping feature has to be enabled at the server level (it is by default by the way) for it to actually make your local drive letters appear in my computer folder of the Windows 2003 terminal server, but even if that particular feature is turned off, enabling this checkbox sometimes also makes the clipboard work.

This is also a great way to copy something directly from your computer to your local machine when at a client site without having to bundle it up on some FTP server or web site to be downloaded. (Obviously, you’ll still want to zip or otherwise compress the files before you do the copy and paste to avoid unnecessarily transmitting large amounts of data).

I’ve tested this with Windows 2003 64-bit terminal servers and simply turning on that checkbox makes clipboard file transfers work.

Some caviats / tips to keep in mind:

  1. Make sure you’re running the latest RDP Client.  Go to http://www.microsoft.com/downloads and search for "RDP Client" — as of this writing the most recent version was 10/15/2004. 
  2. Your TS Session will become significantly less responsive while the file transfer is in place – that shouldn’t be a surprise – it’s moving a lot of data.
  3. If you select a file, then go edit / copy or press CTRL+C and then flip to an explorer window on the other machine (doesn’t matter what the source is or what the destination is btw) and then right-click in that explorer window, the file copy will start happening as part of the right-click event and will have to complete transferring the file before it displays the right-click menu. 
    1. So avoid doing a right-click copy then right-click paste, or right-click to create a folder before pasting.  Create your destination folder first, then copy the file, then paste the file using CTRL+V or you’ll be stuck waiting for the entire file transfer to take place before the right-click menu appears.
  4. You will get a "warning" on connecting that information on your local drives will be available to the TS session, but that’s kind of the whole point you want to be able to move files to/from your machine.
  5. For some reason the rdpclip.exe process that manages the RDP clipboard (including for file transfers) can sometimes become unresponsive in TS, especially on Windows 2003 terminal servers.  If that happens, just end the RDPClip.exe process, for your user account only, and then startà Run rdpclip.exe again to reset it.  After you do that the clipboard will work again (even for file transfers).

Here’s a little batch file you can edit to automate the process of killing the rdpclip.exe process for just your user account, then launching it when it’s killed. Copy this into a file called something like "ResetRDPClip.bat" then put a shortcut to it on your quick launch bar or desktop to make it easy to use:

@echo off
taskkill /f /FI "USERNAME eq DOMAIN\UserName" /im rdpclip.exe
echo "About to restart the rdpclip.exe task … (pause here to not kill new task)"
start rdpclip.exe

Important: don’t forget to change the DOMAIN\UserName to your domain name & username and DO NOT remove the pause — you need to let the taskkill process finish before you start the rdpclip process again or you’ll end up with no RDPClip process running at all.