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Is it possible to control Server2's screen in this situation? Even if only to detatch from it.
The only thing I could see to do was tell Server1's screen to kill its window containing the SSH session.
Yes, it is possible. One of the commands you can send Screen with its metacharacter (^A) is a literal ^A, which is done with the ^A-a (ctrl-A, lowercase a) sequence. On the help screen (^A-?), you will see one key defined as meta.
So, in short, to send a command to a screen within a screen (e. g. to disconnect the nested screen), you would press ^A-a-d, which would send ^A-d to the nested screen, detaching it and leaving the first-layer screen connected.
