Hi Amanda:
Adagio can be configured to send emails 3 ways: [1] MAPI (your current setting), [2] Direct (goes directly to your email server, bypasses Outlook), [3] Outlook (available in Payables 9.3A; does not ask for permission on every email).
The configuration can be different for each user. Therefore I suggest looking at how the other users have configured their systems (go to their computer(s), run Payables, look for the "Email" option on the main screen and "Email setup" on the menu.
You can configure your system the same way. Or, even simpler, if you have a current version of Payables, you can try the "Outlook" option.