What you’re seeing is the Remote Desktop client asking for permission to redirect local resources like printers and drives into the remote session. This prompt can start appearing after a Windows update, a change in Remote Desktop client settings, a new connection profile, or if you’re connecting to a different host or through a different method such as an .rdp file or Remote Desktop app. There’s also the possibility of a policy change on the remote system or your local machine. If group policy was updated, it can force prompting for redirected resources even if your local settings say otherwise. It’s essentially a security safeguard, so it wants you to explicitly confirm what your local machine is allowed to share with the remote system.
To stop having to recheck those boxes every time, you need to save the settings in your RDP configuration. Open Remote Desktop Connection by running mstsc. Before connecting, click “Show Options,” then go to the “Local Resources” tab. Under “Local devices and resources,” check “Printers” and click “More…” to select “Drives” or any specific drives you want available. After selecting what you need, go back to the “General” tab and click “Save As” to save an .rdp file with those settings. In the future, launch your session using that saved file instead of starting from scratch.
If you’re already using an .rdp file and still getting prompted, it may not be storing those preferences. You can edit the file directly by opening it in a text editor and ensuring these lines are present:
redirectprinters:i:1
redirectdrives:i:1
Save the file and use it to connect again. If your environment is managed by an organization, group policy settings on either your local machine or the remote host might be forcing that prompt regardless of your saved preferences, in which case the behavior can’t be permanently suppressed without administrative changes.
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hth
Marcin