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SMTP virtual server reports 535+5.7.3+Authentication+unsuccessful to Office365 account RRS feed

  • Question

  • Hello - We have a SMTP virtual server on our database server that sends database notification emails - I'm unable to get emails to send successfully.  The SMTP log files shows I am getting "535+5.7.3+Authentication+unsuccessful"

    Specs are Windows Server 2012 R2, SQL Server 2017 and IIS6 plugin for SMTP Virtual Server

    • I've checked the login to office365 by going to office online, and I can login to the account.
    • Test emails sent from the database server end up in the <mailroot>\queue folder but never are deleted (sent)
    • I've tried manually adding an email test file into <mailroot>\pickup and those are immediately moved to the queue folder, where they stay
    • All of the records in the log file show the first part of the connection to Office365 but then the "535+5.7.3+Authentication+unsuccessful" result.
    • On the IIS 6 (SMTP Virtual server), I have verified the setup using this:  https://support.office.com/en-us/article/how-to-configure-iis-for-relay-with-office-365-eb57abd2-3859-4e79-b721-2ed1f0f579c9
    • I've tried changing the port from 587 to port 25 and then back again.  The same issue with the "535+5.7.3+Authentication+unsuccessful"

    Does anyone have a recommendation for what I should try next?

    Thank you,

    Ann

    Tuesday, April 24, 2018 7:39 PM

All replies

  • Hi,

    Thanks for your question.

    Please try the following link to see if it helps.

    https://confluence.atlassian.com/jirakb/office365-smtp-configuration-receives-authentication-errors-646250764.html

    Highly appreciate your effort and time. If you have any questions and concerns, please feel free to let me know. 

    Best regards,

    Michael 


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    Wednesday, April 25, 2018 2:53 AM