Is there a way to prevent me from sending out emails to greater than a certain number of people? I don't want to accidentally reply all or send to a wrong distribution list. I was wondering if it would be possible to have outlook prompt me if the email I'm about to send is going to more than, let's say 5 people. Does this even make sense? Thanks!
I'm not familiar with the Outlook client, but in any case, beware of mailing lists: It seems pretty much impossible to discern a mailing list from a "normal" recipient (without maintaining a list of all possible mailing lists in your environment).
If that's not a problem for you, it might be possible to write a (VBA?) macro that hooks is invoked when pressing the "send" button, asking you for confirmation if the number of recepients is greater than some predefined value.
This describes how to implement something very similar (it asks for confirmation before sending when the subject line is empty); you should probably be able to modify it accordingly.