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Unable to Send E-mail from Web App via Exchange RRS feed

  • Question

  • Hello,


    I am responsible for a server running Windows Server 2012 R2, which hosts a few purchased web-based applications. One of these applications needs to send notification e-mail messages via our internal Exchange server. I have done the following, but it doesn't work:

    • Received confirmation from the Exchange team that the web server has relay access.
    • Configured the SMTP E-Mail Settings in IIS to point to our Exchange server.
    • Installed SMTP service on the Web server.
    • Configured the Virtual SMTP Server in the IIS 6.0 console - received GeneralFailure from the app.
    • Removed settings from Virtual SMTP Server - app now says the email function succeeded, but nothing has been received.
    • Used telnet to connect to Exchange server to send test message - success.
    • Used telnet to connect to web server locally to send test message - "queued mail for delivery", but never sent.

    The app vendor says the issue is with our SMTP settings. This seems confirmed by the fact that the message fails to send via telnet. I really need to get this fixed.


    Thanks in advance.


    David V ACTI

    Monday, August 7, 2017 6:24 PM

All replies

  • What does the IIS SMTP server's logs say?  You should be able to see successes and failures in SMTP logs.

    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
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    Tuesday, August 8, 2017 12:57 AM
  • Hi,

    Did you see some failure responses in telnet session? Such as “530 5.7.1 Client was not authenticated” or other? 

    To make sure the mail flow exists, you can check the message tracking log by running this command: Get-MessageTrackingLog -EventId Send -Start "x/x/xxxx x:xxAM" -End "x/xx/xxxx x:xxPM" | FL Send*,Recipient*.

    If the Event ID Send exists, you can also check if the Event ID Fail exists.


    Best Regards,

    Manu Meng
    TechNet Community Support


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    Tuesday, August 8, 2017 9:39 AM
    Moderator