Hey guys,

Any ideas on how I should configure my qmt to deal with this kind of
problem? I ran both the swaks and openssl tool and verified that the problem
is with the remote server and not mine.

./swaks --protocol ESMTPS --to [email protected] --from [email protected]

=== Trying mail.domain.ca:25...
=== Connected to mail.domain.ca.
<-  220 mail.domain.ca Microsoft ESMTP MAIL Service, Version: 5.0.2195.6713
ready at  Thu, 25 Feb 2010 17:04:32 -0800
 -> EHLO mail.domain.com
<-  250-mail.domain.ca Hello [192.168.0.254]
<-  250-TURN
<-  250-ATRN
<-  250-SIZE
<-  250-ETRN
<-  250-PIPELINING
<-  250-DSN
<-  250-ENHANCEDSTATUSCODES
<-  250-8bitmime
<-  250-BINARYMIME
<-  250-CHUNKING
<-  250-VRFY
<-  250-TLS
<-  250-STARTTLS
<-  250-X-EXPS GSSAPI NTLM LOGIN
<-  250-X-EXPS=LOGIN
<-  250-AUTH GSSAPI NTLM LOGIN
<-  250-AUTH=LOGIN
<-  250-X-LINK2STATE
<-  250-XEXCH50
<-  250 OK
 -> STARTTLS
<-  220 2.0.0 SMTP server ready
*** TLS startup failed (error:00000000:lib(0):func(0):reason(0))
*** STARTTLS attempted but failed
 -> QUIT


openssl s_client -starttls smtp -crlf -debug -connect mail.domain.ca:25

depth=0 /C=CA/ST=BC/L=Vancouver/O=domain/OU=Exchange/CN=PC/emailAddress=
[email protected]
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 /C=CA/ST=BC/L=Vancouver/O=domain/OU=Exchange/CN=PC/emailAddress=
[email protected]
verify error:num=27:certificate not trusted
verify return:1
depth=0 /C=CA/ST=BC/L=Vancouver/O=domain/OU=Exchange/CN=PC/emailAddress=
[email protected]
verify error:num=21:unable to verify the first certificate
verify return:1
write to 0x109cb080 [0x109dc610] (75 bytes => 75 (0x4B))
0000 - 16 03 01 00 46 10 00 00-42 00 40 86 91 60 c6 2f   ....f.....@..`./
0010 - f0 84 6a 33 0f 28 12 b4-c7 95 0f 17 25 5b 8a ac   ..j3.(......%[..
0020 - 5b 5a ff 1b b6 87 2f 66-ee 44 e6 5a f7 14 6f bc   [Z..../f.D.Z..o.
0030 - bf b7 88 b9 73 ca 52 76-43 f6 9e 7b 66 4f 13 d6   ....s.RvC..{fO..
0040 - 14 e6 a4 0d ab 3b 83 bf-b4 4c 03                  .....;...L.
write to 0x109cb080 [0x109dc610] (6 bytes => 6 (0x6))
0000 - 14 03 01 00 01 01                                 ......
write to 0x109cb080 [0x109dc610] (37 bytes => 37 (0x25))
0000 - 16 03 01 00 20 11 2e 1f-cd 99 a7 15 f7 f9 86 95   .... ...........
0010 - b6 8f 42 e9 f1 e0 f3 26-43 32 b0 65 7f 03 2f ea   ..B....&C2.e../.
0020 - 63 e7 d2 3f d2                                    c..?.
read from 0x109cb080 [0x109d19b0] (5 bytes => 0 (0x0))
4665:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake
failure:s23_lib.c:188:

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