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SMTP Relay and Automated emails RRS feed

  • Question

  • ***Please do not recommend using the Office 365 SMTP relay setup. This method is very limited and would be fine for simple setups. There is a limit on how many emails that can be sent a day and how fast they are sent.  Any type of “Burst” mail will get stuck. So this is not an option for most of what we are doing.  I am already using that setup for other apps now.

    I am trying to figure out how to completely remove my old exchange server but I can’t until I solve this little problem. I have automated apps that send emails.  These used to go to our old exchange server and be relayed without any problems. Since we are removing the old exchange server I need a different way to handle this.

    On the old Internal exchange server I had to setup connectors to forward all the relay mail to Microsoft (frontbridge). Any mail that was sent to @MYDOMAIN.COM was sent correctly. Now with that server going away I am trying to get the relayed mail that is being sent to @MYDOMAIN.COM to relay from the new 2008r2 SMTP relay server.

    So, I setup an internal SMTP server to handle this traffic. The problem that I am seeing is any emails that were sent to the @MYDOMAIN.COM are failing. They go to every other domain just fine. This is ONLY effecting emails that are being generated from within our INTERNAL network and going to the external hosted servers (Microsoft 365).

    Example:
    An internal email is generated and is sent to bob@external.com = The external user gets that email.
    An internal email is generated and is sent to me@mydomain.com = It fails getting to me
    An internal email is generated and is sent to me@mydomain.onmicrosodt.com and it works just fine also

    ***Yes, my internal domain does not have the same name as the external one.
    ***Oh, and the little gem on this is we host our own web sites in our DMZ

    website1@MYDOMAIN.COM
    website2@MYDOMAIN.COM
    website3@MYDOMAIN.COM


    I think I have narrowed the problem down to DNS (Maybe). When I try to send an email from the relay server it just sees the @MYDOMAIN.COM and stops. It never looks up the external MX records. Is this correct, if so how do I fix this?

    Thanks for any input or direction you can give me



    • Edited by jjmacdonald Friday, March 16, 2012 12:52 PM View
    Friday, March 16, 2012 12:50 PM

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