What do you mean by "classification" here - looking at Outlook's ribbon, the closest concept I see is the categories button & dropdown; is that the same thing? If it is, yes it would be possible to set a category when the no-reply-all button
was pressed, but what would prevent the user from removing it before forwarding or replying (say, on some device that pays no attention to the no-reply-all, etc. flags)? Would it be robust enough to do what you want?
Would it be easier to maintain two distribution lists - internal people, and everybody (the latter including the former list as one entry, so that you don't repeat names)? Would it be as easy to choose the appropriate list as to set a classification or no-reply-all?
Let me see if I understand the scenario: you have some distribution lists which include both internal and external people, but sometimes you want to send messages (meeting requests only, or other message types too?) to just internal people; and you're currently
using a heuristic of calendar entry and no signature to block the propagation, yes? What is it that's blocking the send - some server-side rule? (Sorry, I'm definitely not an Exchange expert, so don't know how these things work.) And what you really want is
to set a flag on the message/calendar entry (your classification/category) as a more explicit means of indicating that the message should be internal only; and you want to tie setting that classification to the no-reply-all button as a convenience? Is that
right, or am I misinterpreting?