Tim
(@tneville)
Hi Laura,
Can you provide us a copy of your diagnostics log from PostSMTP please?
Kind Regards,
Tim
Where would I find this? I have the session transcript but I am not seeing a general diagnostics log.
Tim
(@tneville)
Hi Laura,
Sorry, it’s under Post SMTP > Post SMTP > Diagnostic Test. It is under the ‘Troubleshooting’ heading.
Kind Regards,
Tim
I found it. Is there a way to send it to you privately?
Tim
(@tneville)
Hi Laura,
I’m afraid not. Not to worry, we can run through a few things.
Can I confirm that the sender address in Post SMTP matches exactly the email address of the actual sender account in 365?
Kind Regards,
Tim
I can confirm. I am using the exact same email address.
Tim
(@tneville)
Hi Laura,
Thanks for checking that. Just checking that the mailbox/user also does not have two-factor authentication (TFA) enabled?
Have you tried disabling, and re-enabling ‘Authenticated SMTP’ in the Office 365 Admin Centre. The location of that option is in my original post.
Kind Regards,
Tim
Yes, the mailbox does have TFA enabled. Is it still possible to do this with this enabled, like I do with Gmail? I can go ahead now and try disabling and reenabling ‘Authenticated SMTP’.
Tim
(@tneville)
Hi Laura,
Ah, okay. With TFA enabled you will need to generate an ‘App Password’ for PostSMTP. This will enable PostSMTP to connect to 365 with it’s own unique password and will bypass the TFA.
Here’s a guide on how to set up an App Password in 365:
https://docs.microsoft.com/en-us/azure/active-directory/user-help/multi-factor-authentication-end-user-app-passwords#create-and-delete-app-passwords-from-the-additional-security-verification-page
I’m updating my guide to include this now, as I appreciate this is not clear.
Please let us know how you get on. 🙂
Kind Regards,
Tim
Ok. That makes sense. I think I did do that with Gmail too, it’s just been a while and I didn’t remember. Thanks. I’ll update the ticket after I do that.
Tim
(@tneville)
Hi Laura,
No problem – these things can often get missed! 🙂
I’ll look out for your reply later on.
Kind Regards,
Tim
Hi Tim,
Apparently App Password functionality has been retired from 365 and replaced with Microsoft Authenticator. I did not get a chance to figure out how we might connect the SMTP plugin using the new method because it turns out the email deliverability was another issue altogether and we found a different solution.
I don’t have many clients using 365 but if I do, I imagine I’ll need to explore this further.
Thanks for your help!
Laura
Tim
(@tneville)
Hi Laura,
That’s strange – normally Microsoft Docs are quite up-to-date, and at a glance I can’t see anything about that.
Since the last reply, the developer has now released an extension for the Office 365 API which might be a good fit for your scenario. It is currently free of charge.
https://postmansmtp.com/extensions/office-365-for-post-smtp-extension/
Kind Regards,
Tim
