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Authenticating to outgoing mail server

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  • Authenticating to outgoing mail server

    I am trying to get a remote user on an SBS 2003 to be able to use the companies outgoing SMTP server and I seem to have hit a stumbling block. I have done this before with another SBS 2003 customer. His persoanl ISP ( seems to be on a blacklist or two according to GFI MailEssentials.

    I started working with the SBS organizations adminstrator account using Outlook Express on my desktop any my home location for testing. The outgoing mail server is configured to authenticate first and uses the same credentials as the incoming mail server.

    In the SMTP relay properties on the SBS server, I have check off to allow authenticated users to realy regardless of the list. When I try an e-mail, I am prompted for a password to send an e-mail and the administrator pasword is rejected.

    Any ideas what I might me overlooking? As I mentioned, I have this same senario working on another customer.

    Network Engineers do IT under the desk

  • #2
    Re: Authenticating to outgoing mail server

    So, based on your selection, an authenticated user (administrator) should relay.
    Since "Allow all computers witch successfully authenticate..." is not checked you have to specify clearly witch users or groups are allowed the relay.
    Both “Submit permission” and “Relay permission” options should be selected. (See my screenshot)
    Attached Files
    Csaba Papp
    MCSA+messaging, MCSE, CCNA
    Remember to give credit where credit is due and leave reputation points where appropriate


    • #3
      Re: Authenticating to outgoing mail server

      Thanks for the reply Netxt. My settings are now the same as yours except in my case, the authenticated user is the administrator with both send and relay permissions.

      In Outlook Express on my network I have the e-mail account set up as the administrator on the other account I am trying to realy through.

      I can pull the e-mail from the administrator's account with the incomming mail server, but when I try to send an e-mail through an authentication windows in Outlook Express pops up asking for the password for administrator and the domain name.

      In the account setting in Outlook Express I have 'outgoing mail server requires authentication' and I also checked off the the authentication is the same as the incomming mail server.

      This one has me stumped
      Network Engineers do IT under the desk


      • #4
        Re: Authenticating to outgoing mail server

        I seemed to have blindly stumbled accross the solution. It seems only the administrator account can't relay. Any other Domain User can. This would explain why I was successful in setting this up before with another customer who's remote users needed POP access.

        The only reason I was using the administrator account was just to run the preliminary test. Also, I am dealing with Small Business Server 2003 which has its own inherent set of secuity characteristics.

        Thanks for the suggestions
        Network Engineers do IT under the desk