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IIS Smtp Relay using Smarthost

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  • IIS Smtp Relay using Smarthost


    I currently have this configuration:

    4 servers, each 1 role from exchange 2007

    mailbox, hub, client access, edge

    i added an extra server with 2003 r2 x64 standard so i could install GFI MailSecurity and GFI MailEssentials. on this server i configured mail relay for our domain.

    Everything works fine when i send a mail from the domain (outlook and owa)

    put when i replay from an external domain, the message never comes thru and i receive on the external account: authentication failed

    i've struggled many days to figure this out and i've came at the end of the line!

    i've tried removing the edge subscription and working only with the iis smtp relay but it's the same effect!

    help would be really appreciated!!

    thanks in advance!


  • #2
    Re: IIS Smtp Relay using Smarthost

    Way did not install GFI on you edge server???

    Exchange 2007 HUB request authentication and TLS.
    Configure you new smtp relay to authenticate and start TLS when it forward email to your Exchange server.

    But again, if your GFI product support Exchange 2007, it is better to install them on you edge server.
    Csaba Papp
    MCSA+messaging, MCSE, CCNA
    Remember to give credit where credit is due and leave reputation points where appropriate


    • #3
      Re: IIS Smtp Relay using Smarthost

      i'm not quit sure why i did i taught it was the best solution

      i got the mail working but now i have an other problem!

      when i use exchange or OWA: i can send and receive! works perfectly!!

      now i would like to configure POP3 and SMTP
      on the EDGE i have made a new connector with extra IP address so i could use port25 BUUUUUT i always get "error user not autheticated" on the client!

      pop3 is no problem, only SMTP!

      when i select anonymous authetication, it works!
      off course i would like to use authentication, but it always fails!

      on the other hand, when i add the same user on the edge (same username and password as in domain) it works!!

      so i think ADAM is f*cking with me??


      • #4
        Re: IIS Smtp Relay using Smarthost

        When using POP3 and SMTP in Exchange 2007, you have to use port 587 for client to server SMTP authentication. Microsoft is going towards port 25 for Server to Server communications and 587 for Client to Server communications. If you go to the Receive Connector, you will see the Server connector is using port 25 while the Client connector is using port 587.


        • #5
          Re: IIS Smtp Relay using Smarthost

          my ports are configured correctly, everything works fine (even thru port 25 and 587) the only thing that isn't working is the authentication:

          i doesn't authenticate automatically, i need to add the user and it's password locally also!!