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Question : Are dcc chat/get/sends window session specific?

No, i believe they are session independant, and i think custom windows should act in the same manner that these do. While i am not sure i like the idea of multiple custom windows of the same name, it would be an improvement if custom windows were treated in the same fashion that chat/get/send windows are.

Maybe a flag for the window command could be added that would, when used, create a session specific custom window. This custom window would only be manipulated by events/aliases/scripts that are called from the occumpanying session, unless scon scid etc is used. And, as a session specific window, it could then allow other custom windows of the same name to be created, either session specific to other sessions, or a session independant one (limit of 1 independant and 1 per session dependant), where the order of processing first checks session specific custom windows, and finally uses the session independant window if not previously matched to a session specific window.... ok, going on a bit now, but you get the idea... i think this would avoid breaking existing scripts, while improving on the behavior of custom windows and making them a little more uniform to other session independant windows.

As for $window, it should remain session specific, and should infact list all session dependant windows followed by all session independant windows. (which is how is currently works). The above mentioned idea would, if implemented correctly into a script, avoid the problem of listing all custom windows.