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I am having a very unique situation here and hopefully someone can help me to resolve this issue.I am using a windows laptop and using RDP to jumpbox to authenticate new domain first after that from this jumpbox I need to open another RDP session to windows client machine to get some work done .everything is fine untill this point but if I try to run any Tasks as admin elevation (such as running cmd as admin ,or uninstalling programs , changing IP address of the client machine etc.) it requires CRTL ALT DEL and and it doesnt work at all .

if I do CRLT ALT DEL it works on my own laptop .if I do CRTL ALT END it works for jump box which is the first hop but for the second RDP session it only works if I bring up Windows On screen keyboard however OSK is not a prefered method and I was wondering if there is any other way to get this done ? Maybe we can assign a different key combination other than CRTL ALT DEL in second hop or create a shortcut on the desktop so it would the same thing.

Any thoughts or idea about this issue ?

slowshell
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    I'm confused, why would running Windows apps as admin require you to press Ctrl-Alt-Del? – Ryan Bolger Apr 29 '20 at 04:08
  • Use the On-Screen-Keyboard on the N-1 system to send a ctrl-alt-delete or control-alt-end as needed. Though you almost never actually need to send a ctrl-alt-delete if you start things correctly. – Zoredache Apr 29 '20 at 05:40
  • `OSK is not a prefered method` Why? – Greg Askew Apr 29 '20 at 15:13
  • Ryan Bolger I am using standard user account to login second Windows VM and if I want to do run Windows cmd as admin ,CRTL ALT DEL notification cause Windows UAC is enabled by default .We can disable UAC but that creates a huge security risk on our side and we wouldnt want to go with that route . – slowshell Apr 29 '20 at 19:03
  • Greg Askew second VM will be the users day to day work done environment so they just dont find using OSK is practical solutions. – slowshell Apr 29 '20 at 19:05

2 Answers2

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I just ran into a similar situation and was able to get it to work with sticky keys. Hit the shift button 5 times in a row and a pop up asking to enable sticky keys will appear on each machine being controlled. Click no on your local machine and the first RDP server, but then yes on the second RDP server. Now just tap ctrl, alt, and then delete one at a time. Only the machine with sticky keys enabled will receive the command.

Bryon
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The only way I was able to do it is by using the visual keyboard on the first remote desktop and then type the ctrl+alt+end.

Lady Dragonfruit
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