Assistance with SMTP errors RRS feed

  • Question

  • Morning, I have been using the smtp.office365.com service for quite some time without issues. Starting a while back, I started getting the following error so I can no longer use this. I have been using it as my primary smtp point because ours (which uses anonymous and port 25) frequently drops messages and says it cannot find a email account for a subscriber, not the same one all the time.

    send-mailmessage : The SMTP server requires a secure connection or the client was not authenticated. The server
    response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
    At line:1 char:1
    + send-mailmessage -from scom@xxx -to myemailaddress -subje ...
    + ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
        + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpExcept
        + FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessag

    I have a SMTP server installed on my primary Mgmt server with it configured to send to that service.

    I am using a email account that has send/receive rights and TLS port 587. I use the following PS to check that port communications work.

    test-netconnection smtp.office365.com -port 587

    ComputerName     : smtp.office365.com
    RemoteAddress    :
    RemotePort       : 587
    InterfaceAlias   : Ethernet0
    SourceAddress    :
    TcpTestSucceeded : True

    Any ideas, suggestions greatly appreciated.


    Friday, August 7, 2020 12:19 PM

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