WF Email Configuration Issues with Office 365

posted on January 23, 2024

Hello, I'm trying to configure WF Email server to use an O365 account but I'm getting an error.

""The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail. Error: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator."

I've confirmed that SMTP Auth is enabled for the email account I'm trying to use and I was able to connect the email account to my outlook and send an email to myself from the account so I know the account can send and receive emails.

Does anyone have a guide or whitepaper for setting up WF with Office 365 accounts? Like a list of all the security settings that need to be checked for this to work?

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replied on January 23, 2024 • Show version history

This issue is purely on the Microsoft side. This post response from Microsoft suggests a Azure AD / Entra ID Conditional Access policy could still be blocking "Legacy Authentication" for the user even if SMTP AUTH is enabled for it in O365:

https://learn.microsoft.com/en-us/answers/questions/512954/535-5-7-139-authentication-unsuccessful

https://learn.microsoft.com/en-us/exchange/troubleshoot/email-delivery/fix-issues-with-printers-scanners-and-lob-applications-that-send-email-using-off#error-authentication-unsuccessful (#4)

I'd start by checking/trying that.

"the request did not meet the criteria to be authenticated successfully" certainly sounds like a Conditional Access policy block to me.

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