Send Ctrl-Alt-Del to nested RDP session

Use the On-Screen Keyboard (osk.exe). You can press Ctrl-Alt-Del virtually!

(Note: you may need to hold the CTRL and ALT keys on your physical keyboard (Windows Server 2012-R2))

I found a way to make this work. I frequently work with nested RDP sessions that go in several levels deep. That's just how I prefer to work, especially with lots of VMs.

Keep in mind that my environment is primarily Windows 7 and Server 2008 R2.

Here's the scenario: I RDP from Computer A to Computer B and from Computer B to Computer C.

1. If I want to send Ctrl+Alt+Del to Computer A, I type Ctrl+Alt+Del from Computer A

2. If I want to send Ctrl+Alt+Del to Computer B, I type Ctrl+Alt+End from Computer A

3. If I want to send Ctrl+Alt+Del to Computer C, I open the On-Screen Keyboard on Computer B and use it to type Ctrl+Alt+End, which sends Ctrl+Alt+Del to Computer C

4. If I try to use the On-Screen Keyboard to send Ctrl+Alt+Del on ANY of those three machines, it refers me to the Start menu, which does not help me at all.

So, to send Ctrl+Alt+Del to a remote machine, simply use the OSK to send Ctrl+Alt+End from the session just before the remote machine you are trying to send it to. Works every time.

You can also create a shortcut that performs the CTRL-ALT-DEL action for you (very useful in environments where OSK is not accessible.) Create a shortcut to the following:

C:\Windows\explorer.exe shell:::{2559a1f2-21d7-11d4-bdaf-00c04f60b9f0}

Double-click that shortcut to access the CTRL-ALT-DEL screen.

Set both RDP sessions to Send Windows keys to remote window.

Now, to send Ctrl-Alt-Del to the first session, use Alt-Ctrl-Del. To send commands to the second window, use Alt-Ctrl-End.