Seems Adobe is selecting the first or default profile. I don't think Adobe is Outlook-aware, it just uses the default mail client with the default profile. When you start Outlook, in the selection list, the profile shown as default, is it the same as the one Adobe selects? If it is then try this: Change the default profile to another one, then send with Adobe. If it selects the new profile then you have proof that Adobe selects the default profile, not the current one.