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SMTP email accounts require signing in again
Question asked by ASB Admins - 1/10/2023 at 3:24 PM
Unanswered
Hello, 

I was wondering if anyone else has a problem with having to sign in the email accounts with OAuth2 every so often. It doesn't seem like there's a pattern. Is this required by SmarterTrack or is it Microsoft. I can't find anything when searching. Thanks!

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Kyle Kerst Replied
Employee Post
SmarterTrack's OAuth integration should not be requiring this of you, and it sounds like you may be encountering an issue with the authentication token that was issued. What is prompting the OAuth re-authentication process; are you seeing SMTP/POP logs that indicate the authorization has expired? 

I did a fairly extensive deep dive into O365 setup and configuration to test these integrations but I don't remember seeing a setting or configuration that might limit the length of time on that side either. I am going to do a little poking around though to see if I can find something on Microsoft's side that might govern this and I'll let you know what I find!
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
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ASB Admins Replied
Thanks Kyle. Yes, I notice that messages are not being sent in the spool. Then I look in the logs and it says unauthorized. No rhyme or reason to it.
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Kyle Kerst Replied
Employee Post
Interesting! I didn't find anything on the O365/Microsoft side that would cause these tokens to expire sooner, so we might need to take a closer look. Can I get a ticket started with you so we can dig into it further?
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
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ASB Admins Replied
Yeah, that would be great!
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Kyle Kerst Replied
Employee Post
Done :-) We'll update here once we find the root cause as well so anyone else who runs into this in the future can resolve it as well. Talk to you soon!
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
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Artur Rzasa Replied
For our setup, we only use OAuth for POP.. and have left SMTP with the basic auth as they haven't disabled that at this point. From reading, they didn't want to risk breaking many hardware devices that can't do OAuth authentication.
And seems they really just wanted to reduce the risk to users with receiving emails like MFA/2FA codes, password resets.

I know that doesn't fix the SMTP OAuth issue for you, but if going back to SMTP with basic auth resolves for now, it may be better. You could leave a test queue with SMTP OAuth while you investigate with ST team.
-- Art
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ASB Admins Replied
Good to know Artur. Support and I haven't figured anything out as it's not happening yet again. But I'll check into going back to basic.

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