When setting up e-mail and something fails, it'd be very helpful to get the verbose session transcript to see what's happening. Thus far I'm unable to get FindIT to send via Office 365 despite copying/pasting credentials and server info.
BTW, the same exact credentials work fine to send e-mail from an IMAP/SMTP account setup in Outlook 2016.
Also, I see where you're giving the reply information I was looking for previously, I didn't wait long enough for the second bar to show. I recommend removing the first "Failed to send to..." bar and just said "Failed: REASON HERE" in a single bar.
It's also interesting that another Cisco beta device I'm testing also fails to send via Office 365's smtp servers. That said, RV325 and ISA570W devices can connect and send using smtp.office365.com without issue. The biggest difference I see is in FindIT and the other device we have options of the type of authentication where the RV325 and ISA570W do not. However, those devices are authenticating is how FindIT needs to be able authenticate.
This is a closed forum... I want to know what I am missing out on darnit! no secret squirrels please LOL