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failure sending mail: 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

  • 1.  failure sending mail: 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

    Posted Mar 04, 2020 11:43 PM
    Hello,

    Getting error after changing sender address email for SSRS reports:

    failure sending mail: 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 [MN2PR13CA0026.namprd13.prod.outlook.com]Mail wil

    Where do I enter credentials for the account used in sender address?
    Do I need to setup relay or any other setup I might missed?

    thank you!!



    ------------------------------
    Alicja
    ------------------------------


  • 2.  RE: failure sending mail: 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

    TOP CONTRIBUTOR
    Posted Mar 05, 2020 07:34 AM
    I do not know if this applies to SQL 2014 or not. I have 2018. But SMTP is configured outside of reporting services in SQL Server Management Studio. Expand Management once you've connected to your server, and under Management is Database Mail.



    ------------------------------
    Kyle Hardin
    NAV Developer
    ArcherPoint Inc.
    Duluth GA
    ------------------------------



  • 3.  RE: failure sending mail: 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

    Posted Mar 05, 2020 11:33 AM
    Are you using office365?
    If so, then secure your email with an internal smtp relay installed on IIS.
    or Office365.

    settings would be:
    smtp.office365.com
    Encryption: tls/ssl
    port: 587
    user: email
    pass: yourpass


    ------------------------------
    Roger Neely
    OOBE
    Greenville
    ------------------------------



  • 4.  RE: failure sending mail: 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

    Posted Mar 05, 2020 12:35 PM
    Hello Roger,
    Thank you! Yes, using office 365, could you please let me know where would I need to change those settings at?
    thanks!!

    ------------------------------
    Alicja
    ------------------------------



  • 5.  RE: failure sending mail: 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

    TOP CONTRIBUTOR
    Posted Mar 06, 2020 07:51 AM
    Those settings go where I said in my first reply. SQL Server Management Studio.

    ------------------------------
    Kyle Hardin
    NAV Developer
    ArcherPoint Inc.
    Duluth GA
    ------------------------------



  • 6.  RE: failure sending mail: 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

    Posted Mar 06, 2020 03:42 PM
    Thanks Kyle!
    I did that, and I did receive the test email but the report still failing, same error as before

    ------------------------------
    Alicja
    ------------------------------



  • 7.  RE: failure sending mail: 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

    Posted Mar 07, 2020 04:24 AM
    Hi Alicja,
    If you are using SQL Server 2014 than you will not be able to use Office 365 directly as it does not support SMTP authentication. If you can make SMTP Relay server and use Office 365. SQL Server 2017 support SMTP authentication.

    Or you can use any email server like hMail Email Server to shoot email from your SSRS Services.


    Thank You



    ------------------------------
    KEYUR THAKKAR
    Manager-IT
    BEST VALUE CHEM PVT LTD
    VADODARA
    ------------------------------



  • 8.  RE: failure sending mail: 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

    Posted Mar 09, 2020 05:56 PM
    Hello Keyur,

    thank you for the message!
    correct, I'm on SQL Server 2014, setting it up on Database mail is not working and I don't have the option in IIS to setup SMTP there either..
    can you please let me know how do I setup smtp relay for this?

    thank you!

    ------------------------------
    Alicja
    ------------------------------



  • 9.  RE: failure sending mail: 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

    Posted Mar 10, 2020 08:44 PM
    Hello,

    I have gmail account setup with sendgrid smtp relay, I can send as the other email account from gmail no problem, but the SQL subscriptions are still failing





    can you please let me know what else I am missing?

    thank you!


    ------------------------------
    Alicja
    ------------------------------



  • 10.  RE: failure sending mail: 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

    Posted Mar 11, 2020 12:05 AM
    Hi Alicja,

    You are trying to send email as an anonymous without authentication, which is not supported by Office 365 or Gmail. As i said in my earlier reply, SQL Server 2014 Reporting services does not support SMTP Authentication, so you wont be able to send email using these settings.

    You can setup SMTP Relay Server and try sending email from it. Please read below page for more detailed information about how to send email from Office 365 from an application.


     SMTP Relay Server Guidelines


    ------------------------------
    KEYUR THAKKAR
    Manager-IT
    BEST VALUE CHEM PVT LTD
    VADODARA
    ------------------------------



  • 11.  RE: failure sending mail: 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

    SILVER CONTRIBUTOR
    Posted Oct 22, 2021 12:37 PM
    Hello NAVUG / D365UG,

    For those of you who are struggling with this TLS1.2 and Microsoft Office 365 issue and are on an older version of NAV...

    We are on NAV2017, SQL server 2016

    This blog solved it for us, scroll down to "Best Answer"
    Sql-server – Enable TLS 1.2 for SQL Server 2016 database mail – iTecTec

    I was successful in testing from both NAV RTC SMTP settings and SQL Database Email setup

    Hope this helps others.

    ------------------------------
    Michael Sedlock
    VP of I.T.
    Dukal Corporation
    Ronkonkoma NY
    ------------------------------



  • 12.  RE: failure sending mail: 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

    TOP CONTRIBUTOR
    Posted Mar 11, 2020 08:05 AM
    Upgrade the SQL server to something that can do modern encryption and authentication.Your options are extremely limited since you can't authenticate the first SMTP hop.

    ------------------------------
    Kyle Hardin
    NAV Developer
    ArcherPoint Inc.
    Duluth GA
    ------------------------------



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