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Hi Brian!

You are right, there was once a feature request about shadowing sessions. I believe you can do it semi-automatic with a task. Create a task with the following configuration:

Task Name: Shadow
Command: cmd.exe
Arguments: /V:ON /C "QUERY session /server:$Host$&SET /P uinp=Enter Session ID to shadow and press [ENTER]:&shadow !uinp! /server:$Host$"
Working Directory: %windir%\system32

[here the link to the description of the shadow command: http://technet.microsoft.com/en-us/library/bb490803.aspx]

This task should display all available sessions and asks you for the ID you want to shadow, afterwards the shadow command will be executed.

I haven't really tested this task, so it would be great if you could get back to us on that.

cheers

Stefan