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Can you specify the connection to reconnect to in Terminal Server?

You can utilize the TSCON command to connect to a active or disconnected session.

Reference: http://support.microsoft.com/kb/321703

I did find a warning about consoles being unlocked from this command so you may also want to look at this article: http://support.microsoft.com/kb/302801

I did notice that in testing, this transfers the connection to your console and ends the connection with the client that the user in logged in on.

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