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Re: SASL vs. M$ Outlook and Outlook Express

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  • mouss
    ... - enable both PLAIN and LOGIN - telnet to your postfix and see what it offers (forward the result here) - post the output of postconf -n - try sending
    Message 1 of 25 , Jan 1, 2007
      Tom Kovar wrote:
      > I have tried it with enabling PLAIN and LOGIN, nothing changed. If I
      > remove PLAIN and have only LOGIN, the Outlook client exits immediately,
      > stating that the server does not offer a mechanism supported by Outlook
      > - so this will not be the problem, either.
      >


      - enable both PLAIN and LOGIN
      - telnet to your postfix and see what it offers (forward the result here)
      - post the output of 'postconf -n'
      - try sending mail with outlook. post the corresponding logs

      > Btw., with IMAP, Outlook sends "AUTH PLAIN" without any problem...
      >

      This is unrelated. IMAP != ESMTP.
    • Michael Wang
      ... I fiddled with Outlook 2002 (don t have Express) and my Postfix setup which is also running Dovecot for both IMAP and SASL and the only way I was able to
      Message 2 of 25 , Jan 1, 2007
        Tom Kovar wrote:
        > As stated in my previous mail - offering LOGIN as authentication
        > mechanism does not change anything on the problem. Offering both PLAIN
        > and LOGIN does not change anything, offering only LOGIN leads to an
        > error message by the client that the server does not offer any mechanism
        > supported by Outlook Express. (After initial failure with both Outlook
        > and O.Express, I continue testing only with Express now).
        >
        > So frankly I do not believe that Outlook Express really supports LOGIN
        > mechanism...

        I fiddled with Outlook 2002 (don't have Express) and my Postfix setup
        which is also running Dovecot for both IMAP and SASL and the only way I
        was able to get the Outlook not to send the AUTH command is if I turned
        off the "My Outgoing server (SMTP) requires authentication" check box.
        Are these Windows machines that are trying to connect personal machines
        or are they setup in some sort of managed environment where perhaps
        something is overriding that setting? I don't know enough about Outlook
        to suggest where to look for that sort of thing.

        Oh and Outlook 2002 does handle PLAIN only (but it prefers LOGIN if both
        are offered) so that's definitely not the issue.

        --
        Michael Wang
      • Magnus Bäck
        On Monday, January 01, 2007 at 14:32 CET, ... No, that s not okay. The Microsoft-style LOGIN mechanism is missing. More recent Microsoft clients may support
        Message 3 of 25 , Jan 1, 2007
          On Monday, January 01, 2007 at 14:32 CET,
          Rene van Hoek <rene@...> wrote:

          > I did an telnet to your machine and that seems ok:
          >
          > Leto:/Volumes renevanhoek$ telnet mail.kovarovi.org 25
          > Trying 194.212.102.169...
          > Connected to bimbo.kovarovi.org.
          > Escape character is '^]'.
          > 220 mail.kovarovi.org ESMTP Postfix
          > EHLO test.a8.nl
          > 250-mail.kovarovi.org
          > 250-PIPELINING
          > 250-SIZE 10240000
          > 250-VRFY
          > 250-ETRN
          > 250-AUTH PLAIN
          > 250-AUTH=PLAIN
          > 250-ENHANCEDSTATUSCODES
          > 250-8BITMIME
          > 250 DSN

          No, that's not okay. The Microsoft-style LOGIN mechanism is missing.
          More recent Microsoft clients may support the PLAIN mechansim as well,
          but since people may be running older software I'd say it's a
          requirement to provide both PLAIN and LOGIN.

          While the OP is fixing LOGIN, I suggest he fixes support for CRAM-MD5
          and DIGEST-MD5 as well so that clients won't be forced to send passwords
          in the clear.

          [...]

          --
          Magnus Bäck
          magnus@...
        • Tom Kovar
          So, thank you all. Problem solved, it is really the LOGIN method, that is required for SMTP SASL. But the key thing is the broken_sasl_auth_clients story,
          Message 4 of 25 , Jan 1, 2007
            So, thank you all.
            Problem solved, it is really the LOGIN method, that is required for SMTP
            SASL. But the key thing is the "broken_sasl_auth_clients" story, i.e.
            what matters is the **order** of proposed methods. The M$ clients really
            need to see 250-AUTH=LOGIN in the message.

            What I tried earlier was dovecot proposing methods "PLAIN" and "LOGIN".
            This leads to the SMTP server response to client's EHLO message
            250-AUTH=PLAIN LOGIN
            which is not recognised by the M$ clients (without any comment or
            message, anyway) - even if broken_sasl_auth_clients is set to yes all
            the time. If my dovecot proposes the methods in the reversed order, i.e.
            "LOGIN" and "PLAIN", Bill Gates seems satisfied.

            My love towards this damned Micro$oft grows stronger and deeper. Cashing
            big money for delivering scrap. Well well.

            Once again, thanks for the extensive help.

            Best regards,
            --- Tom

            -----Original Message-----
            From: owner-postfix-users@...
            [mailto:owner-postfix-users@...] On Behalf Of Tony Earnshaw
            Sent: Monday, January 01, 2007 3:09 PM
            To: postfix-users@...
            Subject: Re: SASL vs. M$ Outlook and Outlook Express


            Tom Kovar wrote:

            > I have tried it with enabling PLAIN and LOGIN, nothing changed. If I
            > remove PLAIN and have only LOGIN, the Outlook client exits
            immediately,
            > stating that the server does not offer a mechanism supported by
            Outlook
            > - so this will not be the problem, either.

            Oh yes, it is. We have MS Outlook Express and Outlook clients and they
            connect without problems. Do two things:

            1: telnet mail.barlaeus.nl 25
            ehlo mydomain.net

            See what it says.

            2: openssl s_client -starttls smtp -connect mail.barlaeus.nl:25

            See what it says.

            You need the "AUTH=LOGIN" for the MS client to recognize it. You
            therefore need broken_sasl_auth_clients = yes in main.cf.

            > Btw., with IMAP, Outlook sends "AUTH PLAIN" without any problem...

            What the bleeding heck does that have to do with the price of fish?

            --Tonni

            --
            Tony Earnshaw
            Email: tonni at hetnet.nl
          • Tom Kovar
            Yeah, Magnus, very much right. But not only that: LOGIN apparently has to be the **FIRST** method proposed by the server - if not, M$ does neither find nor
            Message 5 of 25 , Jan 1, 2007
              Yeah, Magnus, very much right. But not only that: LOGIN apparently has
              to be the **FIRST** method proposed by the server - if not, M$ does
              neither find nor recognise it.

              Tack så mycket,
              --- Tom

              -----Original Message-----
              From: owner-postfix-users@...
              [mailto:owner-postfix-users@...] On Behalf Of Magnus Bäck
              Sent: Monday, January 01, 2007 7:00 PM
              To: postfix-users@...
              Subject: Re: SASL vs. M$ Outlook and Outlook Express


              On Monday, January 01, 2007 at 14:32 CET,
              Rene van Hoek <rene@...> wrote:

              > I did an telnet to your machine and that seems ok:
              >
              > Leto:/Volumes renevanhoek$ telnet mail.kovarovi.org 25
              > Trying 194.212.102.169...
              > Connected to bimbo.kovarovi.org.
              > Escape character is '^]'.
              > 220 mail.kovarovi.org ESMTP Postfix
              > EHLO test.a8.nl
              > 250-mail.kovarovi.org
              > 250-PIPELINING
              > 250-SIZE 10240000
              > 250-VRFY
              > 250-ETRN
              > 250-AUTH PLAIN
              > 250-AUTH=PLAIN
              > 250-ENHANCEDSTATUSCODES
              > 250-8BITMIME
              > 250 DSN

              No, that's not okay. The Microsoft-style LOGIN mechanism is missing.
              More recent Microsoft clients may support the PLAIN mechansim as well,
              but since people may be running older software I'd say it's a
              requirement to provide both PLAIN and LOGIN.

              While the OP is fixing LOGIN, I suggest he fixes support for CRAM-MD5
              and DIGEST-MD5 as well so that clients won't be forced to send passwords
              in the clear.

              [...]

              --
              Magnus Bäck
              magnus@...
            • Tom Kovar
              So, thank you all. Problem solved, it is really the LOGIN method, that is required for SMTP SASL. But the key thing is the broken_sasl_auth_clients story,
              Message 6 of 25 , Jan 1, 2007
                So, thank you all.
                Problem solved, it is really the LOGIN method, that is required for SMTP
                SASL. But the key thing is the "broken_sasl_auth_clients" story, i.e.
                what matters is the **order** of proposed methods. The M$ clients really
                need to see 250-AUTH=LOGIN in the message.

                What I tried earlier was dovecot proposing methods "PLAIN" and "LOGIN".
                This leads to the SMTP server response to client's EHLO message
                250-AUTH=PLAIN LOGIN
                which is not recognised by the M$ clients (without any comment or
                message, anyway) - even if broken_sasl_auth_clients is set to yes all
                the time. If my dovecot proposes the methods in the reversed order, i.e.
                "LOGIN" and "PLAIN", Bill Gates seems satisfied.

                My love towards this damned Micro$oft grows stronger and deeper. Cashing
                big money for delivering scrap. Well well.

                Once again, thanks for the extensive help.

                Best regards,
                --- Tom


                -----Original Message-----
                From: owner-postfix-users@...
                [mailto:owner-postfix-users@...] On Behalf Of Tony Earnshaw
                Sent: Monday, January 01, 2007 3:09 PM
                To: postfix-users@...
                Subject: Re: SASL vs. M$ Outlook and Outlook Express


                Tom Kovar wrote:

                > I have tried it with enabling PLAIN and LOGIN, nothing changed. If I
                > remove PLAIN and have only LOGIN, the Outlook client exits
                immediately,
                > stating that the server does not offer a mechanism supported by
                Outlook
                > - so this will not be the problem, either.

                Oh yes, it is. We have MS Outlook Express and Outlook clients and they
                connect without problems. Do two things:

                1: telnet mail.barlaeus.nl 25
                ehlo mydomain.net

                See what it says.

                2: openssl s_client -starttls smtp -connect mail.barlaeus.nl:25

                See what it says.

                You need the "AUTH=LOGIN" for the MS client to recognize it. You
                therefore need broken_sasl_auth_clients = yes in main.cf.

                > Btw., with IMAP, Outlook sends "AUTH PLAIN" without any problem...

                What the bleeding heck does that have to do with the price of fish?

                --Tonni

                --
                Tony Earnshaw
                Email: tonni at hetnet.nl
              • Bill Landry
                ... The order presented doesn t matter. I have: 220 mail.inetmsg.com - INetMsg ESMTP Mail Service - UCE Not Permitted! ehlo test.net 250-mail.inetmsg.com
                Message 7 of 25 , Jan 1, 2007
                  Tom Kovar wrote the following on 1/1/2007 10:06 AM -0800:
                  > Yeah, Magnus, very much right. But not only that: LOGIN apparently has
                  > to be the **FIRST** method proposed by the server - if not, M$ does
                  > neither find nor recognise it.

                  The order presented doesn't matter. I have:

                  220 mail.inetmsg.com - INetMsg ESMTP Mail Service - UCE Not Permitted!
                  ehlo test.net
                  250-mail.inetmsg.com
                  250-PIPELINING
                  250-SIZE 10240000
                  250-ETRN
                  250-AUTH PLAIN LOGIN
                  250-AUTH=PLAIN LOGIN
                  250-ENHANCEDSTATUSCODES
                  250-8BITMIME
                  250 DSN
                  quit
                  221 2.0.0 Bye

                  and it works fine with both Outlook and Outlook Express clients.

                  Bill
                • Tony Earnshaw
                  Magnus Bäck wrote: [...] ... Yep ... Sending passwords in the clear can be avoided with TLS c.q. SSL. Also, unfortunately at the last count (beta
                  Message 8 of 25 , Jan 1, 2007
                    Magnus Bäck wrote:

                    [...]

                    > No, that's not okay. The Microsoft-style LOGIN mechanism is missing.
                    > More recent Microsoft clients may support the PLAIN mechansim as well,
                    > but since people may be running older software I'd say it's a
                    > requirement to provide both PLAIN and LOGIN.

                    Yep

                    > While the OP is fixing LOGIN, I suggest he fixes support for CRAM-MD5
                    > and DIGEST-MD5 as well so that clients won't be forced to send passwords
                    > in the clear.

                    Sending passwords in the clear can be avoided with TLS c.q. SSL.

                    Also, unfortunately at the last count (beta < 1) Dovecot didn't support
                    CRAM-MD5 or DIGEST-MD5 - just as it didn't support many of the things
                    that are possible with Cyrus and on the IMAP level Courier
                    IMAP/maildrop. Getting CRAM-MD5 and DIGEST-MD5 to work with Postfix (at
                    least with Cyrus SASL) means using auxprop and in our case with an LDAP
                    base, ldapdb.

                    I'd be happy to learn that things on the Dovecot front have improved
                    since last April or so and that it now does support both, though without
                    LDAP-based maildrop (and the underlying authlib service) the mail
                    service that we offer at our site would be impossible.

                    --Tonni

                    --
                    Tony Earnshaw
                    Email: tonni at hetnet.nl
                  • James Turnbull
                    ... Hash: SHA1 ... Only the 1.0 release candidates support CRAM-MD5 and DIGEST-MD5. I can say that I have been running RC15 in a couple of places as
                    Message 9 of 25 , Jan 1, 2007
                      -----BEGIN PGP SIGNED MESSAGE-----
                      Hash: SHA1

                      Tony Earnshaw wrote:
                      > Also, unfortunately at the last count (beta < 1) Dovecot didn't support
                      > CRAM-MD5 or DIGEST-MD5 - just as it didn't support many of the things
                      > that are possible with Cyrus and on the IMAP level Courier
                      > IMAP/maildrop. Getting CRAM-MD5 and DIGEST-MD5 to work with Postfix (at
                      > least with Cyrus SASL) means using auxprop and in our case with an LDAP
                      > base, ldapdb.

                      Only the 1.0 release candidates support CRAM-MD5 and DIGEST-MD5. I can
                      say that I have been running RC15 in a couple of places as production
                      without issue. YMMV. I've also had no issues with the LDAP backend for
                      authentication - though that's not in production for us.

                      Regards

                      James Turnbull

                      - --
                      James Turnbull <james@...>
                      - ---
                      Author of Pro Nagios 2.0
                      (http://www.amazon.com/gp/product/1590596099/)

                      Hardening Linux
                      (http://www.amazon.com/gp/product/1590594444/)
                      - ---
                      PGP Key (http://pgp.mit.edu:11371/pks/lookup?op=get&search=0x0C42DF40)
                      -----BEGIN PGP SIGNATURE-----
                      Version: GnuPG v1.4.6 (MingW32)
                      Comment: Using GnuPG with Mozilla - http://enigmail.mozdev.org

                      iD8DBQFFmYEC9hTGvAxC30ARAk1BAKCGThP2jc9/V6olnNGSkn4KE4v7rQCfZZEu
                      vno8BpHeWSWcVBH6Ah9fYMg=
                      =Wc17
                      -----END PGP SIGNATURE-----
                    • Robert Schetterer
                      ... Hi, i have postfix, saslauthd , mysql, dovecot running on many servers ( suse 10.1), i have no problem, using outlook express, outlook, thunderbird (
                      Message 10 of 25 , Jan 1, 2007
                        Michael Wang schrieb:
                        > Tom Kovar wrote:
                        >> As stated in my previous mail - offering LOGIN as authentication
                        >> mechanism does not change anything on the problem. Offering both PLAIN
                        >> and LOGIN does not change anything, offering only LOGIN leads to an
                        >> error message by the client that the server does not offer any mechanism
                        >> supported by Outlook Express. (After initial failure with both Outlook
                        >> and O.Express, I continue testing only with Express now).
                        >>
                        >> So frankly I do not believe that Outlook Express really supports LOGIN
                        >> mechanism...
                        >
                        > I fiddled with Outlook 2002 (don't have Express) and my Postfix setup
                        > which is also running Dovecot for both IMAP and SASL and the only way I
                        > was able to get the Outlook not to send the AUTH command is if I turned
                        > off the "My Outgoing server (SMTP) requires authentication" check box.
                        > Are these Windows machines that are trying to connect personal machines
                        > or are they setup in some sort of managed environment where perhaps
                        > something is overriding that setting? I don't know enough about Outlook
                        > to suggest where to look for that sort of thing.
                        >
                        > Oh and Outlook 2002 does handle PLAIN only (but it prefers LOGIN if both
                        > are offered) so that's definitely not the issue.
                        >
                        Hi,
                        i have postfix, saslauthd , mysql, dovecot running on
                        many servers ( suse 10.1), i have no problem, using
                        outlook express, outlook, thunderbird
                        ( latest versions )
                        whatever pop3, imap, imaps, pop3s
                        smtp, smtps
                        with virtual domain postfixadmin
                        so in my eyses problems are a configure issue
                        i configured saslauthd to ask imap dovecot with plaintext passwords
                        ( plain is not not nice but needed for other stuff in my case )
                        Regards and happy new year

                        --
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