- Open Remote Desktop and click the Local Resources tab
- Check the Clipboard box and click More...
- Check Drives and click OK
Now when you connect, you will be able to copy and paste files directly from the local machine to the remote machine.
Whereas the clipboard works for copying and pasting basic content such as text (assuming clipboard sharing is enabled), sharing disk drives via the Local Resources tab is the key to being able to seamlessly copy and paste files across Remote Desktop.