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Possible to configure Exchange for SSL SMTP on Port 465?

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  • Possible to configure Exchange for SSL SMTP on Port 465?

    Hi all,

    My ISP is Virgin Media. I currently Smarthost through the old smtp.ntlworld.com SMTP Server (I am ex-NTL). I understand that now most, if not all the Email Address platforms (blueyonder, ntlworld, virgin.net etc) have been migrated to GMail, we are required to start using SSL for SMTP on Port 465.

    I am not sure of how to get Exchange to Smarthost through the new smtp.virginmedia.com Server as I understand Exchange does not play well with SSL SMTP natively. Does anyone know what to do to switch my Smarthost over to the new SMTP Server?

    I know this may sound like a case of "If it ain't broke then don't fix it" but I imagine soon VM will disable smtp.ntlworld.com and so I'd like to switch over in advance to reduce any downtime. The current way it works is a lot easier as the Server authenticates by the IP Address (it must be a VM IP) and that's it - you can use the SMTP.

    Any help is appreciated thanks,

    Karl

  • #2
    Re: Possible to configure Exchange for SSL SMTP on Port 465?

    Hi derelyth,

    It looks like a lot of people are going to be suffering with this problem in the near future.

    After a hunt around the Internet I have found a program called "stunnel" which appears that it will sort this out and enable you to send out fine, but you will need to have the program running all of the time.

    There is a simple how to guide here (it says mail client, but the same rules will probably apply);

    http://www.ehow.com/how_6011431_configure-stunnel.html

    Let me know how you get on with this.

    I am sure for business customers, Virgin will provide a solution.

    Ste
    Steven Roberts
    IT Mercenary

    MCITP:EA|MCTS|MCSE 2003 (Messaging and Security)|MCSA 2003 (Messaging and Security)|MCP|Prince2 Practitioner

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    • #3
      Re: Possible to configure Exchange for SSL SMTP on Port 465?

      If your ISP truly is using GMail then they should also support TLS on port 587 for outbound email to their smarthost, and as far as I know Exchange 2003 does natively support TLS without any issues.

      Might be wrong though, never had to configure more than authentication for a smarthost in the past.
      BSc, MCSA: Server 2008, MCSE, MCSA: Messaging, MCTS
      sigpic
      Cruachan's Blog

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      • #4
        Re: Possible to configure Exchange for SSL SMTP on Port 465?

        Thanks for the replies

        Ste - I've actually heard of Stunnel before myself - hadn't thought of it, but it's going to take some reading up before I start messing with it again!

        cruachan - I believe the backend is pure GMail as the Virginmedia webmail interface is now exactly as it is for regular GMail except for the colour-scheme. I did think about running on 587 with TLS because of Exch's native support for it, but as far as configuring the Smarthost to run through 587 to be able to use TLS I have no idea

        As far as the configuration of the Smarthost goes, I have it configured under the Advanced tab of the Default SMTP Virtual Server if that makes any difference as I have seen articles and posts concerning SMTP Connectors, but I am unsure as to whether I need to use that method as the Default Server setup seems to work fine.

        Cheers,

        Karl

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        • #5
          Re: Possible to configure Exchange for SSL SMTP on Port 465?

          Using an SMTP connector is recommended, it's definitely considered better practice than using the SMTP virtual server settings.

          GMail's own SMTP servers require either SSL or TLS so I would expect that third parites using what is effectively Google Apps would be the same. You'll obviously need to confirm that with Virgin Media though.

          I'm not familiar enough with STunnel to make a recomendation there, the only time I've used it is for pulling POP3 email out of GMail and into Exchange. Horrible setup but it works.
          BSc, MCSA: Server 2008, MCSE, MCSA: Messaging, MCTS
          sigpic
          Cruachan's Blog

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          • #6
            Re: Possible to configure Exchange for SSL SMTP on Port 465?

            Thanks again cruachan

            Following your reply, I'll read up on using a Connector to Smarthost my mail through VM and then take it from there.

            I'll return here when I have sorted the Connector

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            • #7
              Re: Possible to configure Exchange for SSL SMTP on Port 465?

              This is easy to do.
              Create a new SMTP virtual server, with the required port number set, instead of port 25.
              Create a new SMTP connector, to use the new SMTP virtual server, and set it to use TLS.
              You may have to set an authentication parameter as well.

              Job done.

              However if they are using the Gmail platform, this may not work as you expect. Gmail rewrite the email addresses based on the account going through. You may well end up having to use a third party to route email through.
              I am also a Virgin Media customer, but I route my email through my own server that lives in a data centre.

              Simon.
              --
              Simon Butler
              Exchange MVP

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              • #8
                Re: Possible to configure Exchange for SSL SMTP on Port 465?

                Ah, thanks Simon, I'll give it a go over the next day or two

                The email rewriting of Gmail is something I have experienced before - when I first tried to smarthost my mail through their SMTP server using my Gmail address as authentication - the emails appeared to be from my own Gmail address

                I'll try the VM route, and see what happens and report back

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