I'm on Sonoma 14.1.1 if that's helpful. Sadly, when I switched to shift-cmd-D in the StreamDeck macro it sends the "D" character to the remote session too....Dclipboard....every time. 

So still not utopia, but another nice workaround. Thanks for pointing it out. I hope you can get it working as well. 

I've not used app shortcuts before! I configured it to use shift-cmd-D and it works without the Essentials menu being expanded. I suspect cmd-v might be conflicting with your system wide default for paste. 

The other solution I've found was picking up an Elgato Stream Deck and creating a button maco that shifts app focus to ScreenConnect, focuses to the menu bar (F9), presses B which highlights the Essentials menu, presses down arrow twice, then hits enter. It works fairly well, but occasionally F9 will stop working and I'll have to fiddle with the keyboard/shortcut settings in System Settings to get it working again.

Replacing F9,B,down,down,enter with the app shortcut key combo you just showed me should make it even better! 

Please make sure the Mac client gets the keyboard shortcut for "Send Clipboard Keystrokes" as well