We just switched to Outlook365 as our mail provider.
Outlook requires an SMTP servername of SMTP.outlook365.com
using port 587 with TLS.

In the Postman Service, this will not work with the "use old implementation" box unchecked...
But it WILL work with both the TLS box AND the "use old implementation" box checked...the TEST email works fine.

However, if you save that configuration, the "TLS" box is somehow cleared (i.e. unchecked for you) and then all of your production email sends fail with "unable to authenticate".

All of my wonderful WatchDirectory email tasks are failing left and right! 

Edited to add: I am using WatchDirectoryPro version 4.8.7

Hello Gert, thank you for the quick reply. I have created an Outlook 365 email account for you and emailed you the password to the email in your signature block.

Thanks!

The correct mail server is always helpful.

I still had an issue with my "production" email account, but the temp email I'd set up for Gert worked perfectly.

It seems someone in the support area of my company reset the password on the WatchDirectory email account and neglected to tell me... 

Everything works perfectly once again, my users are happy and so am I.

I appreciate all the help you have provided Gert!