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What is the best way to realiably send email in an Exchange environment?

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  • What is the best way to realiably send email in an Exchange environment?

    We are getting more and more problems recently with email delivery issues, especially to web based email providers such as hotmail.

    We have tried various methods of delivery - from direct MX delivery to using smarthosts but its becoming more and more frequent that either we or the smarthost we use gets blacklisted, which then causes delivery problems.

    This can be quite an issue for us as we manage several separate systems.

    I am now thinking about using a third party delivery service such as dyn.com, but I am just wondering what other people normally use for mail delivery?
    David Silvester
    Systems Administrator

  • #2
    Re: What is the best way to realiably send email in an Exchange environment?

    I wouldn't look any further than Messagelabs (although since they are "now part of Symantec", I do worry a bit )
    Tom Jones
    MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
    PhD, MSc, FIAP, MIITT
    IT Trainer / Consultant
    Ossian Ltd
    Scotland

    ** Remember to give credit where credit is due and leave reputation points where appropriate **

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    • #3
      Re: What is the best way to realiably send email in an Exchange environment?

      Direct SMTP delivery is easily done, if you have a static IP address, valid PTR and host name and also setup an SPF record.

      Having multiple IP addresses would help, allowing you to give a dedicated address to the Exchange server. That stops you getting blacklisted by stupid users clicking on things they don't.

      I have been direct delivering for years with my ISP Eclipse Internet from my own Exchange server. Most of my clients do as well.

      Using an antispam service is probably the best option, rather than a regular plain smart host service.

      Simon.
      --
      Simon Butler
      Exchange MVP

      Blog: http://blog.sembee.co.uk/
      More Exchange Content: http://exchange.sembee.info/
      Exchange Resources List: http://exbpa.com/
      In the UK? Hire me: http://www.sembee.co.uk/

      Sembee is a registered trademark, used here with permission.

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      • #4
        Re: What is the best way to realiably send email in an Exchange environment?

        I have come across the path of messagelabs on several occasions, I will look into their services.

        Direct MX is ok, but its often caused problems for us - we manage about 40 exchange servers, so its painful when one of them gets blacklisted and we have to spend time cleaning their IP address.

        I just thought perhaps if we handed the delivery over to a third party, it would be another thing that we didn't need to worry about.
        Also we get some clients that do a lot of marketing email - sometimes legitimately, sometimes not. So we also need a system that can help to either regulate that, or at least flag it up if its starting to cause a problem.

        I have also been thinking about setting up a central mailserver that can act as a smarthost to all of our clients, we could have a pool of IP addresses, central management and so on. Just not sure how much of a workload would come laong with that option.
        David Silvester
        Systems Administrator

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        • #5
          Re: What is the best way to realiably send email in an Exchange environment?

          A relay server isn't difficult to setup - you can do it with IIS on a standard Windows 2003 or higher server. Therefore rent a server in a data centre (less than 50/month) and then set it up correctly. Each client would need to have the server in their SPF records for example.

          Stopping blacklisting is pretty easy - block port 25 outbound on the firewall and outsource marketing email delivery. Those two measures alone will deal with most of it. As long as the Exchange servers are setup correctly then you will have no problems.

          Another option would be to subscribe to a antispam service that you can brand as your own and then resell it to your clients. One of my support company clients does that. We still setup everything correctly, so PTR and SPF records on a static IP address, but it is one less thing to deal with.

          Simon.
          --
          Simon Butler
          Exchange MVP

          Blog: http://blog.sembee.co.uk/
          More Exchange Content: http://exchange.sembee.info/
          Exchange Resources List: http://exbpa.com/
          In the UK? Hire me: http://www.sembee.co.uk/

          Sembee is a registered trademark, used here with permission.

          Comment


          • #6
            Re: What is the best way to realiably send email in an Exchange environment?

            Originally posted by Sembee View Post
            A relay server isn't difficult to setup - you can do it with IIS on a standard Windows 2003 or higher server. Therefore rent a server in a data centre (less than 50/month) and then set it up correctly. Each client would need to have the server in their SPF records for example.

            Stopping blacklisting is pretty easy - block port 25 outbound on the firewall and outsource marketing email delivery. Those two measures alone will deal with most of it. As long as the Exchange servers are setup correctly then you will have no problems.

            Another option would be to subscribe to a antispam service that you can brand as your own and then resell it to your clients. One of my support company clients does that. We still setup everything correctly, so PTR and SPF records on a static IP address, but it is one less thing to deal with.

            Simon.
            thats definitely what I want to do.
            Not sure if Ill use windows or Linux though.
            I had originally been thinking of installing cpanel on a linux VM, that way I know its easy to set up multiple IPs and I can then create and assign accounts to different IPs - then just create an email for each account and use that as the SMTP smarthost. that way, its all managed in one place, but also has some redundancy with different clients being on different IP addresses.

            I dont know if it would be possible to do something similar on windows? Either so IPs could be distributed between clients, or so that it would be easy to rotate IPs if one inherited a bad reputation?
            David Silvester
            Systems Administrator

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            • #7
              Re: What is the best way to realiably send email in an Exchange environment?

              I doubt if you will get enough IP addresses for each client to have their own. There is a shortage of IP addresses. I have eight on my own server in a data centre and I am told it is almost impossible to get any more.

              It is rare for the email server to be the actual cause of the problems. In most cases the issue isn't spam going through the server, but a compromised workstation sending messages out directly. If you only have one IP address then everything appears to be coming from the same place.

              Simon.
              --
              Simon Butler
              Exchange MVP

              Blog: http://blog.sembee.co.uk/
              More Exchange Content: http://exchange.sembee.info/
              Exchange Resources List: http://exbpa.com/
              In the UK? Hire me: http://www.sembee.co.uk/

              Sembee is a registered trademark, used here with permission.

              Comment


              • #8
                Re: What is the best way to realiably send email in an Exchange environment?

                Originally posted by Sembee View Post
                I doubt if you will get enough IP addresses for each client to have their own. There is a shortage of IP addresses. I have eight on my own server in a data centre and I am told it is almost impossible to get any more.

                It is rare for the email server to be the actual cause of the problems. In most cases the issue isn't spam going through the server, but a compromised workstation sending messages out directly. If you only have one IP address then everything appears to be coming from the same place.

                Simon.
                I have 5 with my server currently, but my provider makes them available in blocks of 4,8,16 and 32.

                Anyway, I dont want one for each client. Im just thinking, for example, in the past we have often had clients who will send out a load of marketing email without our knowledge, this will then get the IP blacklisted. Just want some redundancy really.
                David Silvester
                Systems Administrator

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