Sage 100 OAuth Password Prompt...every time!

SUGGESTED

I have a Sage 100 end users that is a long time Office 365 user for emailing Paperless Office Documents out of Sage 100.  I am in the process of moving them to OAuth (we are Basic still in our Live Companies).  I had their IT Group perform Steps 1 and 2 of KB 116301 and I completed Step 3 in a Test Company.  I am able to email out of Sage 100 in the Test Company using OAuth, however I receive an Office 365 Email and Password prompt EVERY TIME I email out of Sage 100 (PO, SO, Test from Company Maintenance...it does not matter where I email from, we get the prompt in the Test Company).

I called Sage Support and they recommended the IT person poke around in Office 365 settings but he came up empty.  I guess I have 2 questions:

#1-For those of you that have successfully setup OAuth, do you receive an Office 365 login prompt EVERY TIME you send an email out of Sage 100?

#2-Any idea why we get the Office 365 login prompt EVERY TIME?  Is there some setting you are aware of?

Thanks!