Remote Desktop Gateway running on Server 2008 R2. For starters, I already acknowledge that we are due for hardware upgrade to a later server OS, but that would mean the cost of many Terminal Server licenses just so we can continue to get through the Remote Desktop Gateway to workstations inside the LAN. So the answer, unless someone can point out to me specific known issues, should not be just "upgrade to a modern OS".
I log on to a Windows 10 workstation (on the LAN & on the domain) from my remote/home through my 2008 R2 Remote Desktop Gateway located at the office. I can copy & paste file content but not files. That is, I can highlight & copy text from inside a file on the office computer and paste that into a text editor on my computer, and vice versa. But I cannot copy & paste a file.
On the other hand, I can log onto a Windows 7 computer via RD Gateway on the same network, and there, I can copy and paste files through the remote connection. But yet again, I can log onto the Windows 10 computer directly while connected to the office VPN and copy/paste files just fine.
So the problem of being able to copy/paste text but not copy/paste files is specific to connections 1) to Windows 10 hosts but 2) only when connected through the Remote Desktop Gateway.
What is it in Windows 10 and/or the Remote Desktop Gateway 2008 that will allow me to copy text & files from Windows 7 Host but only text--not files--from Windows 10 host?