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Server 2019 / IIS SMTP Server- Connection error to inbound.protection.outlook.comRSS

3 replies

Last post Jun 17, 2020 09:44 AM by Jalpa Panchal

  • Server 2019 / IIS SMTP Server- Connection error to inbound.protection.outlook.com

    Jun 11, 2020 02:33 PM|Dav3|LINK

    We just migrated our SMTP host server from Server 2008 to Server 2019 in a new data center.

    After the migration I get the following error trying to connect to any clients using outlook.com to host their email. We can send mail to our other clients.

    We don't get bounces our any way to tell why inbound.protection.outlook.com is rejecting our mail because "The remote server did not respond to a connection attempt."

    Here is a snip from the system event logs.

    Message delivery to the host '104.47.0.33' failed while delivering to the remote domain 'hotmail.com' for the following reason: The remote server did not respond to a connection attempt.

    Message delivery to the host '104.47.12.33' failed while delivering to the remote domain 'hotmail.com' for the following reason: The remote server did not respond to a connection attempt.

    "Message delivery to the host '104.47.17.161' failed while delivering to the remote domain 'hotmail.com' for the following reason: The remote server did not respond to a connection attempt.

    "Message delivery to the host '104.47.18.161' failed while delivering to the remote domain 'hotmail.com' for the following reason: The remote server did not respond to a connection attempt.

    "Message delivery to the host '104.47.18.225' failed while delivering to the remote domain 'hotmail.com' for the following reason: The remote server did not respond to a connection attempt.

    Message delivery to the host '104.47.60.36' failed while delivering to the remote domain 'xxxx.com' for the following reason: The remote server did not respond to a connection attempt.

    "Message delivery to the host '104.47.61.36' failed while delivering to the remote domain 'xxxx.ca' for the following reason: The

    Thanks,

    Dave

  • Re: Server 2019 / IIS SMTP Server- Connection error to inbound.protection.outlook.com

    Jun 12, 2020 03:02 AM|Jalpa Panchal|LINK

    Hi,

    Make sure SMTP service is set to manual start and then started manually from either service.msc or from IIS6 manager, e-mail will leave the queue and get delivered to the recipients.

    Refer this below link for more detail:

    https://forums.iis.net/t/1240492.aspx?Windows+Server+2019+Built+in+SMTP+server+not+honoring+MX+records+

    https://forums.iis.net/t/1149291.aspx?SMTP+Send+error

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  • Re: Server 2019 / IIS SMTP Server- Connection error to inbound.protection.outlook.com

    Jun 12, 2020 05:25 PM|Dav3|LINK

    I wish that was true.  I saw that thread before I posted and tried to start inetinfo.exe manually.

    I think my mx records are getting looked up OK.

    Correct me if I am wrong, but isn't 104.47.17.161 a proper mail destination for hotmail.com?

    I think something else in my configuration is wrong?  Any of the inbound.protection.outlook.com mail servers will not respond to a connection request.

    Dave

  • Re: Server 2019 / IIS SMTP Server- Connection error to inbound.protection.outlook.com

    Jun 17, 2020 09:44 AM|Jalpa Panchal|LINK

    I am not sure what destination about you are taking but you could try to set the relay setting:

    Open IIS Manager > Properties > Access tab > Relay Restrictions. Make sure you put at least localhost (127.0.0.1) in the setting.

    https://forums.iis.net/t/1149291.aspx?SMTP+Send+error

    https://docs.microsoft.com/en-us/iis/application-frameworks/install-and-configure-php-on-iis/configure-smtp-e-mail-in-iis-7-and-above

    https://serverfault.com/questions/772739/iis-smtp-server-cannot-send-to-hotmail-outlook-etc-addresses

    also, try to turn off the firewall.

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