Hi Dhanesh, This is a known quirk when using VNC with Guacamole. Even though you've enabled the “send special keys” option and tried tweaking Windows settings and alternative keybindings, sometimes the Windows key combination (specifically Windows + R) doesn't register as expected. Here are a few suggestions to try: - Double-check that no local system hotkeys or application is overriding Windows + R on your client machine. Although other shortcuts work fine, Windows + R is sometimes captured locally by the client OS or even by Guacamole’s browser interface. - Review your Guacamole configuration file for any VNC-related key mapping settings. It might be worthwhile to explicitly define or remap the Windows key. In some cases, adding a...