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Re: SASL vs. M$ Outlook and Outlook Express

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  • Rene van Hoek
    ... We advice our customers to configure outlook in the following way (texts are in Dutch, but the screenshots should be clear):
    Message 1 of 25 , Jan 1, 2007
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      Tom Kovar wrote:
      >
      > --- T
      >
      > -----Original Message-----
      > From: owner-postfix-users@...
      > [mailto:owner-postfix-users@...] On Behalf Of Michael Wang
      > Sent: Monday, January 01, 2007 2:51 PM
      > To: Postfix users
      > Subject: Re: SASL vs. M$ Outlook and Outlook Express
      >
      >
      > Rene van Hoek 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
      >
      > I don't believe Outlook handles PLAIN, I believe it needs to be LOGIN
      > (or NTLM if that's checked in the client), so try modifying your
      > dovecot.conf file and add that to the mechanisms parameter.
      >

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


      We advice our customers to configure outlook in the following way (texts
      are in Dutch, but the screenshots should be clear):

      http://support.active8.nl/index.srf?pkn=file_id&pkv=27&lang_id=360


      I have a Windows machine near me. If you can send me an test-account, I
      would be happy to test if I can authenticate with your mta. I assume you
      don't have an Windows machine currently available?

      By the way, please don't top-post. It makes this thread harder to follow.

      Greetings,

      rene at active8 nl
    • 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 2 of 25 , Jan 1, 2007
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        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.
      • Tony Earnshaw
        ... 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
        Message 3 of 25 , Jan 1, 2007
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          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
        • Rene van Hoek
          ... I am aware that in my configuration, usernames and passwords are sent in clear-text. That is an security-risk, I am aware. On the other hand, I have to
          Message 4 of 25 , Jan 1, 2007
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            Tony Earnshaw wrote:
            > Rene van Hoek 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
            >>
            >>
            >> Also according to the maillog, the client don't authenticate. So the
            >> problem is as far as I can see with the configuration of the client.
            >>
            >> As an test, did you try for yourself to relay mail through your mta
            >> with Windows and Outlook? In this way you can rule-out (or confirm)
            >> client configuration mistakes.
            >
            > MS clients need AUTH LOGIN, PLAIN won't work; also it's a security
            > mistake to offer AUTH PLAIN or LOGIN without first hiding them with
            > smtpd_use_tls = yes and smtpd_tls_auth_only = yes.
            >

            I am aware that in my configuration, usernames and passwords are sent in
            clear-text. That is an security-risk, I am aware.

            On the other hand, I have to deal with a lot of customers which find it
            difficult already to configure their e-mail client in the most simple form.

            I had to balance these two issues and therefore came up with this
            solution for our situation. Don't worry, we don't experience any
            security issues and we monitor our logs closely for unwanted relaying.


            >> Otherwise refer your client to Microsoft Support ;-)
            >
            > After OP has waited his due time and paid his due he'll get to hear the
            > same from them.

            I know, it was also a joke.

            >
            > --Tonni
            >

            Greetings,

            Rene at active8 nl
          • 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 5 of 25 , Jan 1, 2007
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              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 6 of 25 , Jan 1, 2007
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                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 7 of 25 , Jan 1, 2007
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                  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 8 of 25 , Jan 1, 2007
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                    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 9 of 25 , Jan 1, 2007
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                      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 10 of 25 , Jan 1, 2007
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                        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 11 of 25 , Jan 1, 2007
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                          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 12 of 25 , Jan 1, 2007
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                            -----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 13 of 25 , Jan 1, 2007
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                              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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