How to change password over Remote Desktop Connection over Remote Desktop Connection?

We all know the official, documented, and supported way to "change" your password is to press:

• Ctrl + Alt + Del

and then select Change Password.

Except that doesn't work if you are connected to a machine over remote desktop.

We all know the official, documented, and supported way to "change" your password on a remote computer is to press:

• Ctrl + Alt + End

This hotkey combination is sent by the Remote Desktop Client to the server as Ctrl+Alt+Del, causing the option Change Password to appear.

But if you are connected to an RDP session, which is connected to an RDP session, then you cannot use CAD or CAE; because neither reach the final final final computer.

Some people suggest a workaround here is to use the on-screen keyboard inside the RDP window inside the RDP window, and then press Ctrl + Alt + Delete on the on-screen keybaord.

Except we all know that doesn't work:

And the final insult is if you try to go to your account to "change" your password, and it tells you the most unhelpful thing:

How do you change your password on a machine that you are connected to through 2, 3, 4, or more levels of RDP indirection.

Bonus Chatter

I say "change" your password (in quotes), as to distingush it from "resetting" your password.

• the former changes your password
• the latter causes you to lose access to all your certificate private keys, saved passwords, etc

Because you "reset" your old password rather than "change" it, and those private things are encrypted (essentially) with your password.

Solution 1:

We all know that this can be done by running the On-Screen Keyboard on the second-to-last machine, alongside the final Remote Desktop client, and using it to send CtrlAltEnd to the final RDP client – which will then convert it to a Ctrl-Alt-Del on the final machine.

• Machine 0: RDP into machine 1.
• Machine 1: RDP into machine 2.
• Machine 2: Open the On-Screen Keyboard.
• Machine 2: RDP into machine 3. Un-fullscreen the RDP session.
• Machine 2: Use the OSK to press Ctrl-Alt-End.