Sendmail as client via smarthost and ssl

[Christopher Illies]

Thanks for your explanations, Vince. It got me one step further (I think).

<...>

>PLAIN mechanism mean that i'm sending the password/user in plain rather
>than using something like DIGEST-MD5 or any of the other possible
>mechanisms that can be listed in confAUTH_MECHANISMS in your sendmail
>.mc file
>
>to get a list of whats supported by your relay telnet to it on port 25
>and issue an EHLO command. the supported mechanisms are listed following
>the AUTH keyword.
>
>for example for me
>(11:59:59 <~>) 1 $ telnet RELAY.ISP.net 25
>Trying 213.xxx.xxx.53...
>Connected to RELAY.ISP.net.
<...>
>250-AUTH LOGIN PLAIN           ---THIS ONE.
>250-STARTTLS
>250-DELIVERBY
>250 HELP

Ok, when I use telnet, this happens:
> telnet send.ki.se 587
Trying 130.xxx.xxx.26...
Connected to send.ki.se.
Escape character is '^]'.
220 KIMSX09.user.ki.se Microsoft ESMTP MAIL Service ready at Fri, 29 Oct 2010 14:55:51 +0200
EHLO
250-KIMSX09.user.ki.se Hello [136.xxx.xxx.214]
250-SIZE 10485760
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH GSSAPI NTLM      <<<<<<<
250-8BITMIME
250-BINARYMIME
250 CHUNKING


Although I have no idea what GSSAPI and NTLM are, I remembered that I have
seen these abbreviations before: NTLM is an OPTION for cyrus-sasl2, and yes,
it is compiled in (WITH_NTLM=true). And GSSAPI appeared first in the mc file:

define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

So I changed the authinfo/client-info file to:

AuthInfo:[send.ki.se] "U:smmsp" "I:XXX" "P:YYY" "M:GSSAPI"

Still, it does not work:

<<< 530 5.7.1 Client was not authenticated

Christopher