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Re: How best to eliminate "domain mismatch" warning in mail clients when TLS is used

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  • Jeffrey 'jf' Lim
    ... their ... What about using an SNI proxy? Would u have any to recommend? -jf
    Message 1 of 15 , Jul 15, 2013
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      On 16 Jul 2013 03:15, "Wietse Venema" <wietse@...> wrote:

      >
      > Ben Johnson:
      > > On 7/15/2013 1:10 PM, Viktor Dukhovni wrote:
      > > > On Mon, Jul 15, 2013 at 12:47:53PM -0400, Ben Johnson wrote:
      > > >
      > > >> In essence, our clients wish to use their own SSL certificates for their
      > > >> SMTP connections.
      > > >
      > > > Are these submission clients?  What does the above mean?
      > > >
      > >
      > > Yes, these are submission clients. To be clear, our clients want to be
      > > able to configure their MUAs to use our MTA's submission service via
      > > their own domain names. I know; it is not necessarily a rational or
      > > reasonable request.
      >
      > It's entirely reasonable if they want to be able to change email
      > provider without having to update all their clients.
      >
      > Unfortunately there are not a lot of development cycles for adding
      > a decent SNI implementation to Postfix.
      >

      What about using an SNI proxy? Would u have any to recommend?

      -jf

    • Ben Johnson
      ... This is the strongest argument that I ve seen for adding SNI support to Postfix. I hadn t even considered this. Maybe this is the basis for our customers
      Message 2 of 15 , Jul 15, 2013
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        On 7/15/2013 3:14 PM, Wietse Venema wrote:
        > Ben Johnson:
        >> On 7/15/2013 1:10 PM, Viktor Dukhovni wrote:
        >>> On Mon, Jul 15, 2013 at 12:47:53PM -0400, Ben Johnson wrote:
        >>>
        >>>> In essence, our clients wish to use their own SSL certificates for their
        >>>> SMTP connections.
        >>>
        >>> Are these submission clients? What does the above mean?
        >>>
        >>
        >> Yes, these are submission clients. To be clear, our clients want to be
        >> able to configure their MUAs to use our MTA's submission service via
        >> their own domain names. I know; it is not necessarily a rational or
        >> reasonable request.
        >
        > It's entirely reasonable if they want to be able to change email
        > provider without having to update all their clients.
        >

        This is the strongest argument that I've seen for adding SNI support to
        Postfix. I hadn't even considered this. Maybe this is the basis for our
        customers' respective positions; I wish they had made it clearer to
        begin with.

        > Unfortunately there are not a lot of development cycles for adding
        > a decent SNI implementation to Postfix.
        >
        > Wietse
        >

        I can't even imagine the complexities; I understand.

        In the meantime, I am all ears, regarding jf's question about SNI
        proxying via, for example, nginx. If that subject is best addressed to
        the nginx mailing list, I am happy to take the discussion to the
        appropriate list.

        Thanks again,

        -Ben
      • Wietse Venema
        ... According to a thread in March 2013 they did not support SNI in the MAIL feature.
        Message 3 of 15 , Jul 15, 2013
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          Ben Johnson:
          > In the meantime, I am all ears, regarding jf's question about SNI
          > proxying via, for example, nginx. If that subject is best addressed to
          > the nginx mailing list, I am happy to take the discussion to the
          > appropriate list.

          According to a thread in March 2013 they did not support SNI in the
          MAIL feature.

          http://list-archives.org/2013/03/29/nginx-nginx-org/mail-proxy-with-sni/f/1433768745

          Wietse
        • Viktor Dukhovni
          ... There s a lot more to SNI support than having a server that can context-switch between multiple certificates. You need a provisioning system that allows
          Message 4 of 15 , Jul 15, 2013
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            On Mon, Jul 15, 2013 at 03:38:31PM -0400, Ben Johnson wrote:

            > > It's entirely reasonable if they want to be able to change email
            > > provider without having to update all their clients.
            >
            > This is the strongest argument that I've seen for adding SNI support to
            > Postfix. I hadn't even considered this. Maybe this is the basis for our
            > customers' respective positions; I wish they had made it clearer to
            > begin with.

            There's a lot more to SNI support than having a server that can
            context-switch between multiple certificates. You need a provisioning
            system that allows clients to upload private keys and matching
            certificates on a self-service basis via suitably authorized
            administrator accounts.

            You need to send the administrators reminders about iminent
            certificate expiration, and alert your staff if they don't respond
            promptly, so they ultimately get phone calls when they don't act
            in a timely manner.

            The whole thing is a major PITA for very little gain.

            > > Unfortunately there are not a lot of development cycles for adding
            > > a decent SNI implementation to Postfix.

            I have no time for this.

            --
            Viktor.
          • Stan Hoeppner
            ... And this is precisely why an entire VPS industry has sprouted over the past few years. As someone stated down thread, give your customers what they want
            Message 5 of 15 , Jul 15, 2013
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              On 7/15/2013 3:35 PM, Viktor Dukhovni wrote:

              >>> Unfortunately there are not a lot of development cycles for adding
              >>> a decent SNI implementation to Postfix.
              >
              > I have no time for this.

              And this is precisely why an entire VPS industry has sprouted over the
              past few years. As someone stated down thread, give your customers what
              they want and charge them accordingly. This is trivially easy to do
              with your choice of hypervisor with memory consolidation (same page
              merging) and a guest OS template. If your pool of IPv4 addresses is
              limited charge them extra for that. If they're exhausted, well, you can
              go IPv6 only but that really has downsides.

              Here's an even better idea. Do what everyone else in your shoes does:
              partner with a VPS provider and farm the bulk of this out. There are
              tons of small companies that do exactly this. They buy X number of VPS
              instances each with an IP address from a provider and rebrand them. The
              VPS provider does all the heavy lifting WRT provisioning. You would
              simply do the customization for your individual customers, i.e. DNS,
              hostname, domain name, certificate, etc. A basic VPS for this kind of
              thing can normally be had for well less than $10/month. The really
              stripped down VPS services I see offered are $4.95/month. All prices
              USD. If you already have a mailbox (IMAP/POP) server that currently
              handles MX duty for all these customers, moving MX to these VPS
              instances and relaying the mail to your mailbox server is easy as well.

              --
              Stan
            • Peter
              ... Probably the best option is to go old tech here. Get a separate IP for each hostname that a client wants to connect to and set up separate listeners in
              Message 6 of 15 , Jul 15, 2013
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                On 07/16/2013 05:30 AM, Ben Johnson wrote:
                >> If your clients insist that a mail server is only professional if the TLS
                >> session has their domain name written on it, then give them what they want at
                >> the price it costs to implement it.
                >
                > Your position is perfectly reasonable, and is more or less the position
                > that I've taken on the matter. I just wanted to be sure that there isn't
                > some panacea that I had overlooked.
                >
                > In order to give our clients what they want, what are our choices?

                Probably the best option is to go old tech here. Get a separate IP for
                each hostname that a client wants to connect to and set up separate
                listeners in master.cf for each of those IPs with the appropriate TLS
                options. Then let the clients buy their own cert and provide it to you
                to use on the server. Up to you to come up with the additional pricing
                for all of this. The extra dedicated IP is the first and most obvious
                cost, the rest is administrative.

                Keep in mind that you'll have to configure dovecot (or whatever you use
                for IMAP/POP3) to listen on these other IPs and use those
                customer-supplied certs as well.

                Personally I would ramp up the extra fee even more to account for the,
                "I don't want to do this really stupid unnecessary vain thing" reason.
                I would make sure the client knows that they are just spending extra
                money to satisfy their own vanity and if they still want to go ahead
                then do it for them.


                Peter
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