I had a peculiar issue with copying and pasting files from my local computer to a Remote Desktop session. I could copy and paste locally, but the option to paste would be grayed out on the Remote Desktop computer. There are several ways to solve this problem depending on what you are trying to copy and paste.
In Windows 2016, these settings are controlled within Group Policy.
Navigate to “Computer Configuration” > “Administrative Templates” > “Windows Components” > “Remote Desktop Services” > “Remote Desktop Session Host“.
Ensure “Do not allow Clipboard redirection” is set to “Not Configured” or “Disabled“.
Open “Server Manager“.
Select “Remote Desktop” Services.
Select “Tasks“, then choose “Edit Properties“.
Under the “Client Settings” tab, ensure the “Clipboard” and “Drive” is enabled.
Launch “Remote Desktop Session Host Configuration” from the server.
Under “Connections“, right-click the connection and select “Properties“.
Select the “Client Settings” tab, and make sure the “Clipboard” box is unchecked. If you want to allow copying and pasting of files, make sure the Drive selection is unchecked. Click OK when done.
This should be all you need to enable copying and pasting of files to your Remote Desktop session. I hope this tutorial has helped you. Please share your experience in the Comments section below.