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  • Sending email in SBS2008

    Hi Guys and Gals,
    This is my first post. I've googled and binged for an answer for my problem all over the Net, with no luck. I just hope I can find my answer here.

    I have an SBS2008 at my (very small) company. I've been able to configure everything by myself (users, backups, remote access, even the installation of an SSL certificate). However, I'm stuck at the email.

    My problem: I have an external ISP that manages both my website and my email.

    I did not configure my server to handle my website, so I used another domain I bought for it..
    And I don't want to overload my server with email management, so I'm using a POP connector to retrieve several email accounts from my ISP (it works, no problem) and I configured a smart host for sending email.

    The problem: retrieving email from Exchange works; connecting Outlook to Exchange to receive the email also works; but SENDING an email (for instance, replying to a message that was retrieved by Exchange) generates an error message from my ISP, saying that I cannot send email with this configuration.

    Any thoughts and ideas about this are very much welcome!

    Thanks in advance,
    Antonio

  • #2
    Re: Sending email in SBS2008

    What is the exact error message you're getting?

    Originally posted by aemarques View Post
    And I don't want to overload my server with email management
    Begging the question then... how underspecced is your server, that it makes you avoid using SBS the way Microsoft intended it to be used?
    Gareth Howells

    BSc (Hons), MBCS, MCP, MCDST, ICCE

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    • #3
      Re: Sending email in SBS2008

      Are you authenticating to the Smart Host? If not, does your ISP require you to? Have you told them you are using the smart host, some ISPs require this so that they will accept email from your domain. Lastly, are you able to send email outbound with no smart host configured?
      BSc, MCSA: Server 2008, MCSE, MCSA: Messaging, MCTS
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      • #4
        Re: Sending email in SBS2008

        Originally posted by gforceindustries View Post
        What is the exact error message you're getting?



        Begging the question then... how underspecced is your server, that it makes you avoid using SBS the way Microsoft intended it to be used?
        Hi.
        Thanks a lot for tying to help me out.

        I'll try to translate the message in the morning - it is in Portuguese.

        Regarding the server. It is not a problem of power. It is a nice machine (8 GB RAM, Intel quad core, 2x750 GB/RAID1 WD RE2 disks, Gigabit NIC...). However, I want to use it mainly for:
        - Shares/backups
        - Remote access
        - Email / OWA

        However, I don't have a fixed IP address, so it is dangerous to use the SBS2008 as an email server, because these kind of IPs tend to be flagged as spammers.

        I decided to go for SBS2008 / Exchange to do stuff like remote email access through OWA and to share some of our email accounts by several people. Common contacts lists and calendars are also nice...

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        • #5
          Re: Sending email in SBS2008

          Originally posted by cruachan View Post
          Are you authenticating to the Smart Host? If not, does your ISP require you to? Have you told them you are using the smart host, some ISPs require this so that they will accept email from your domain. Lastly, are you able to send email outbound with no smart host configured?
          Hi,
          Thanks for your reply.
          Yes, I'm authenticating the smart host. And no, I can't send anything whithout it. I did told them in advance that I'm using the smart host, but they did not appear to know what I was talking about. Maybe it is time to switch email providers...

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          • #6
            Re: Sending email in SBS2008

            Originally posted by aemarques View Post
            Hi,
            Thanks for your reply.
            Yes, I'm authenticating the smart host. And no, I can't send anything whithout it. I did told them in advance that I'm using the smart host, but they did not appear to know what I was talking about. Maybe it is time to switch email providers...
            Sounds like it. Are you using a business isp? I wouldn't think so judging from what you've already said. Get a decent ISP who will provide a static IP. Personally I only use a smarthost where absolutely necessary.
            BSc, MCSA: Server 2008, MCSE, MCSA: Messaging, MCTS
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            Cruachan's Blog

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            • #7
              Re: Sending email in SBS2008

              It is possible to test this using a 2nd ISP mail server, as long as you have account details for this. I use my home ISP mail server, and username and account to test this quite often. Just change the Outgoing Mail server to one you can auth with, then try that. Failing that I would start to check weather you or your ISP have been flagged on any blacklists.

              Sounds like it. Are you using a business isp? I wouldn't think so judging from what you've already said. Get a decent ISP who will provide a static IP. Personally I only use a smarthost where absolutely necessary.
              While in a perfect world thats a perfect answer, there are sometimes when it is just not possible to get a static IP, be it becuse of cost, law or location.

              We support lots of sites that use a dynamic DNS and a smarthost and we have almost no problem with any of them. We also support plently of SMTP mailsites, and each of them has its advantage and its disadvantage.
              Good to be back....

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              • #8
                Re: Sending email in SBS2008

                could you post us the exact message you get from the ISP?

                At the moment it seems like that's where the configuration error is...
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                • #9
                  Re: Sending email in SBS2008

                  Hi Guys. Thanks a lot for all your help.
                  I managed to solve the problem. There was a mis-configuration between the domain I was using for my website and the domaing used by the ISP to receive and send email, but I have everything up and running now.
                  I also got a static IP from my ISP and published the site for no-hassle remote access.

                  Antonio

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                  • #10
                    Re: Sending email in SBS2008

                    Now that you have a Static IP, are you going to bring the email inhouse? The POP Connector on SBS is really only a temp solution until you get everything sorted out. Remember POP does not encrypt passwords when they are sent.
                    1 1 was a racehorse.
                    2 2 was 1 2.
                    1 1 1 1 race 1 day,
                    2 2 1 1 2

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                    • #11
                      Re: Sending email in SBS2008

                      Good question. I've not consider (yet) bringing the email to the server, because I don't wan't to deal with spam and the added traffic... Is the POP3 connector solution that bad, huh...?

                      Anyway, I have APOP authentication with the POP server which I think will provide at least some sort of protection.
                      Last edited by aemarques; 29th June 2010, 16:54. Reason: Explanation of APOP

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                      • #12
                        Re: Sending email in SBS2008

                        regarding pop, run Wireshark or similar on a device between your server and the pop3 server.
                        even just on your own server if you want,

                        Observe the network stream while the pop connector does it's magic.


                        While it's good to see you're using APOP (personally, I use encrypted SSL pop3 since I'm not in a corporate environment)
                        it's still breachable
                        http://www.mozilla.org/security/anno...sa2007-15.html
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