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As mentioned in this kb article, it is not possible to shadow a session with multiple monitors enabled.

It does mention that

Remote Assistance supports multiple monitors, and is the presently recommended solution if you need this functionality.

My question is, is it possible (and if so, how) to remote assist a terminal services session?

We have a few Windows Server 2008 R2 Terminal Servers running with about 10 or so users that use 2 monitors. It would be ideal to be able to remote into their session but have yet to find a viable solution.

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What solution(s) have you tried already? What happens when you try to use Remote Assistance how you want to? Are you looking to jump into a user's active session without their interaction? –  Ƭᴇcʜιᴇ007 Sep 20 '12 at 20:25
Haven't really tried any solutions; have just been rummaging around the interwebs looking to see what other people have tried, and surprisingly haven't been able to come up with anything. I've come across one or two 'solutions' using XenApp from Citrix but would prefer not to spend any money on additional products if we really don't need to. Ideally we'd be able to use the "Advanced connection option for help desk, type in the server name, and select the session (user), with possibly the only user interaction being "Yes, I accept the request for remote assistance." –  cbergman Sep 20 '12 at 20:35

1 Answer 1

up vote 1 down vote accepted
  • Install Remote Assistance on the server in question and you can control individual sessions – even with multiple monitors.

  • When offering Remote Assistance, click Help someone who has invited you, click Advanced connection option for help desk

  • Type in the name of the server that you installed Remote Assistance on (the server you want to control sessions on), click Next

  • Then it will ask you which session you would like to offer assistance to.

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