SMTP / Office 365 - failing

Hello, last Friday after working successfully for many years, our SMTP settings for Office 365 failed.

As an IT company ourselves, we are very familiar with Office 365.

We are going round in circles.

(1) We enter the correct credentials and QuickFile sends an activation code (which oddly goes into Junk)

(2) We put the activation code into QuickFile and it says “successfully activated”

(3) We try to send an email and we get an error report by email saying the sending failed.

Please see attached PDF with screenshots of the steps above.

Thank you.

QuickFile SMTP Error.pdf (78.3 KB)

Hi @waltmanc

Sorry to hear you’re experiencing some issues here.

I’m not overly familiar with Office / Microsoft 365, but I did find this which may help?

Thank you. We’ve managed to resolve the issue.

@waltmanc Could you share how you resolved this, I’m having a similar issue although not with 365
Thanks

The issue was complex:
Microsoft has changed its security and we needed to create an “app password” to allow SMTP authentication and allow that method in the User settings on Office 365.
We had also restricted our Office 365 tenant only to authenticate with UK IP addresses, but Quickfile uses Microsoft Azure servers based in Ireland, so we needed to modify our Conditional Access Policy to allow Irish IPs.

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Thanks very much!, that’s great

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