Outlook 2003 and TLS

  • Thread starter Thread starter Chris Miller
  • Start date Start date
C

Chris Miller

I'm running Outlook 2003 (SP3).

The server is offering "250 - STARTTLS" and Outlook 2003 has a checkbox
"This server requires an encrypted connection (SSL)" We all know that
SSLV3 is approximately TLSV1 but "approximately" in the encryption world in
never close enough. Can Outlook 2003 participate in TLS? If so, what do I
need to do to make this work?

Please notice that Outlook asks to STARTTLS and the server indicates
readiness to do so but indicates a failure to accept what ever encryption
credentials are presented.

sendmail[1700]: nA73ZVwO001700: <-- STARTTLS
sendmail[1700]: nA73ZVwO001700: --- 220 2.0.0 Ready to start TLS
sendmail[1700]: STARTTLS=server, info: fds=9/3, err=5
sendmail[1700]: STARTTLS=server, error: accept failed=0, SSL_error=5,
errno=0, retry=-1
sendmail[1700]: nA73ZVwO001700: 10.1.2.129 did not issue MAIL/EXPN/VRFY/ETRN
during connection to MSA

Thanks for the help,

Chris.
 
What mail server and version are you running? Reason I ask is that I cannot
duplicate this issue when running a POP3/IMAP connection against Exchange
2003 SP2.
 
neo said:
What mail server and version are you running? Reason I ask is that I
cannot duplicate this issue when running a POP3/IMAP connection against
Exchange 2003 SP2.
Click to expand...

I am running "sendmail". It is the most recent version 8.14.

As you can see, Outlook thinks he has authenticated and tries to undertake
the SMTP dialog starting with "MAIL FROM:"

2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 2.0.0 Ready to start TLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Authorized to host
<========================================================== Outlook 2003
thinks he has authenticated.
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] MAIL FROM: <*****>



But at the same time, sendmail thinks he has not: (Please know that I did
NOT select "POP before SMTP" -- "Log on to incoming server before sending
mail" on the "Outgoing Server" tab of the "Internet E-Mail Settings" dialog.
I DID select, "My outgoing server (SMTP) requires authentication" and
provided the requisite credentials and I DID select "This server requires
and encrypted connection (SSL)" using port 587 in the "Advanced" tab of the
same dialog.)

Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- EHLO File
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-trax.tryx.org
Hello file.tryx.org [10.1.2.129], pleased to meet you
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: ---
250-ENHANCEDSTATUSCODES
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-PIPELINING
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-8BITMIME
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-SIZE
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DSN
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-AUTH DIGEST-MD5
NTLM CRAM-MD5 KERBEROS_V4 GSSAPI
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-STARTTLS
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DELIVERBY
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250 HELP
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- MAIL FROM:
<[email protected]>
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 530 5.7.0
Authentication required <======================================= sendmail
disagrees.






The full logs follow:

2009.11.08 11:38:05 <<<< Logging Started (level is LTF_TRACE) >>>>
2009.11.08 11:38:05 (e-mail address removed): Synch operation started (flags = 00000001)
2009.11.08 11:38:05 (e-mail address removed): UploadItems: 1 messages to send
2009.11.08 11:38:05 (e-mail address removed): Synch operation started (flags = 00000030)
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Begin execution
2009.11.08 11:38:05 (e-mail address removed): DoPOPDownload(flags = 00000030, max msg =
ffffffff): full items
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Begin execution
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Port: 587, Secure: SSL, SPA: no
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Finding host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Connecting to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): ========= Initial blob
=========
2009.11.08 11:38:05 POP3 (pop3.tryx.org):
===================================
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Port: 110, Secure: no, SPA: no
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Finding host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connecting to host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK DBMAIL pop3 server ready
to rock <[email protected]>
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Authorizing to server
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] USER cjm
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Disconnected from host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK Password required for cjm
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] PASS *****
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Port: 587, Secure: TLS, SPA: no
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Finding host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK cjm has 0 messages (0
octets)
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Authorized to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] STAT
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK 0 0
2009.11.08 11:38:05 POP3 (pop3.tryx.org): ==== Comparing server and local
blobs ====
2009.11.08 11:38:05 POP3 (pop3.tryx.org):
==========================================
2009.11.08 11:38:05 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-trax.tryx.org Hello
file.tryx.org [10.1.2.129], pleased to meet you
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-ENHANCEDSTATUSCODES
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-PIPELINING
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-8BITMIME
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-SIZE
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-DSN
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-AUTH DIGEST-MD5 NTLM
CRAM-MD5 KERBEROS_V4 GSSAPI
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-DELIVERBY
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250 HELP
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 2.0.0 Ready to start TLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Authorized to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] MAIL FROM: <*****>
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Do deletions: LoS: no
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Disconnecting from host
2009.11.08 11:38:06 POP3 (pop3.tryx.org): [tx] QUIT
2009.11.08 11:38:06 POP3 (pop3.tryx.org): <rx> +OK see ya later
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Disconnected from host
2009.11.08 11:38:06 POP3 (pop3.tryx.org): ========= No blob changes
=========
2009.11.08 11:38:06 POP3 (pop3.tryx.org):
===================================
2009.11.08 11:38:06 POP3 (pop3.tryx.org): End execution
2009.11.08 11:38:06 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr =
0x00000000
2009.11.08 11:38:06 (e-mail address removed): Synch operation completed
2009.11.08 11:38:22 (e-mail address removed): Task cancelled: flags = 00000001
2009.11.08 11:38:22 SMTP (smtp.tryx.org): Disconnecting from host
2009.11.08 11:38:22 SMTP (smtp.tryx.org): Disconnected from host
2009.11.08 11:38:22 SMTP (smtp.tryx.org): End execution
2009.11.08 11:38:22 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr =
0x80042105
2009.11.08 11:38:22 (e-mail address removed): Synch operation completed
2009.11.08 11:38:22 Resource manager terminated








Nov 8 11:44:42 trax sendmail[7596]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7596]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: <-- \200L\001\003\001
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 500 5.5.1 Command
unrecognized: "
Nov 8 11:44:42 trax dbmail/pop3d[29998]: Message:[serverchild]
serverchild.c,PerformChildTask(+349): incoming connection from [10.1.2.129]
by pid [29998]
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: <-- \001
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 500 5.5.1 Command
unrecognized: "\001"
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 421 4.4.1
trax.tryx.org Lost input channel from file.tryx.org [10.1.2.129]
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: lost input channel from
file.tryx.org [10.1.2.129] to MSA after startup
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax sendmail[7597]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7597]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: --- 421 4.4.1
trax.tryx.org Lost input channel from file.tryx.org [10.1.2.129]
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: lost input channel from
file.tryx.org [10.1.2.129] to MSA after startup
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax dbmail/pop3d[29998]: Message:[pop3] pop3.c,pop3(+440):
user cjm logged in [messages=0, octets=0]
Nov 8 11:44:42 trax sendmail[7598]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7598]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: <-- EHLO File
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-trax.tryx.org
Hello file.tryx.org [10.1.2.129], pleased to meet you
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: ---
250-ENHANCEDSTATUSCODES
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-PIPELINING
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-8BITMIME
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-SIZE
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-DSN
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-AUTH DIGEST-MD5
NTLM CRAM-MD5 KERBEROS_V4 GSSAPI
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-STARTTLS
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-DELIVERBY
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250 HELP
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: <-- STARTTLS
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 220 2.0.0 Ready to
start TLS
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, info: fds=9/3, err=5
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, error: accept
failed=0, SSL_error=5, errno=0, retry=-1
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax sendmail[7599]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7599]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- EHLO File
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-trax.tryx.org
Hello file.tryx.org [10.1.2.129], pleased to meet you
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: ---
250-ENHANCEDSTATUSCODES
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-PIPELINING
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-8BITMIME
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-SIZE
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DSN
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-AUTH DIGEST-MD5
NTLM CRAM-MD5 KERBEROS_V4 GSSAPI
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-STARTTLS
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DELIVERBY
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250 HELP
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- MAIL FROM:
<[email protected]>
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 530 5.7.0
Authentication required
 
I have done a more detailed analysis of the logs and I think I see what is
happening. Outlook starts the encrypted connection and apparently is
unaware that this fails, because sendmail logs this and Outlook does not.
Outlook, unaware of the failure of STARTTLS, somehow re-establishes a
connection to sendmail and continues with normal SMTP niceties: Please
notice "[tx] EHLO File", assumes himself to be authenticated and proceeds on
that basis. So from Outlooks point of view, everything looks fine:

2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 2.0.0 Ready to start TLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Authorized to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] MAIL FROM: <*****>




Meanwhile sendmail has issued the following complaints and summarily reset
the connection to Outlook:

Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: <-- STARTTLS
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 220 2.0.0 Ready to
start TLS
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, info: fds=9/3, err=5
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, error: accept
failed=0, SSL_error=5, errno=0, retry=-1
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA





Logs: (identical to previous post, but included her for completness.)
2009.11.08 11:38:05 <<<< Logging Started (level is LTF_TRACE) >>>>
2009.11.08 11:38:05 (e-mail address removed): Synch operation started (flags = 00000001)
2009.11.08 11:38:05 (e-mail address removed): UploadItems: 1 messages to send
2009.11.08 11:38:05 (e-mail address removed): Synch operation started (flags = 00000030)
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Begin execution
2009.11.08 11:38:05 (e-mail address removed): DoPOPDownload(flags = 00000030, max msg =
ffffffff): full items
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Begin execution
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Port: 587, Secure: SSL, SPA: no
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Finding host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Connecting to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): ========= Initial blob
=========
2009.11.08 11:38:05 POP3 (pop3.tryx.org):
===================================
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Port: 110, Secure: no, SPA: no
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Finding host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connecting to host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK DBMAIL pop3 server ready
to rock <[email protected]>
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Authorizing to server
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] USER cjm
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Disconnected from host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK Password required for cjm
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] PASS *****
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Port: 587, Secure: TLS, SPA: no
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Finding host
2009.11.08 11:38:05 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK cjm has 0 messages (0
octets)
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Authorized to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): Connected to host
2009.11.08 11:38:05 POP3 (pop3.tryx.org): [tx] STAT
2009.11.08 11:38:05 POP3 (pop3.tryx.org): <rx> +OK 0 0
2009.11.08 11:38:05 POP3 (pop3.tryx.org): ==== Comparing server and local
blobs ====
2009.11.08 11:38:05 POP3 (pop3.tryx.org):
==========================================
2009.11.08 11:38:05 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-trax.tryx.org Hello
file.tryx.org [10.1.2.129], pleased to meet you
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-ENHANCEDSTATUSCODES
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-PIPELINING
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-8BITMIME
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-SIZE
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-DSN
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-AUTH DIGEST-MD5 NTLM
CRAM-MD5 KERBEROS_V4 GSSAPI
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250-DELIVERBY
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 250 HELP
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] STARTTLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 2.0.0 Ready to start TLS
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Securing connection
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] EHLO File
2009.11.08 11:38:06 SMTP (smtp.tryx.org): <rx> 220 trax.tryx.org ESMTP
Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Authorized to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): Connected to host
2009.11.08 11:38:06 SMTP (smtp.tryx.org): [tx] MAIL FROM: <*****>
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Do deletions: LoS: no
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Disconnecting from host
2009.11.08 11:38:06 POP3 (pop3.tryx.org): [tx] QUIT
2009.11.08 11:38:06 POP3 (pop3.tryx.org): <rx> +OK see ya later
2009.11.08 11:38:06 POP3 (pop3.tryx.org): Disconnected from host
2009.11.08 11:38:06 POP3 (pop3.tryx.org): ========= No blob changes
=========
2009.11.08 11:38:06 POP3 (pop3.tryx.org):
===================================
2009.11.08 11:38:06 POP3 (pop3.tryx.org): End execution
2009.11.08 11:38:06 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr =
0x00000000
2009.11.08 11:38:06 (e-mail address removed): Synch operation completed
2009.11.08 11:38:22 (e-mail address removed): Task cancelled: flags = 00000001
2009.11.08 11:38:22 SMTP (smtp.tryx.org): Disconnecting from host
2009.11.08 11:38:22 SMTP (smtp.tryx.org): Disconnected from host
2009.11.08 11:38:22 SMTP (smtp.tryx.org): End execution
2009.11.08 11:38:22 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr =
0x80042105
2009.11.08 11:38:22 (e-mail address removed): Synch operation completed
2009.11.08 11:38:22 Resource manager terminated








Nov 8 11:44:42 trax sendmail[7596]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7596]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: <-- \200L\001\003\001
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 500 5.5.1 Command
unrecognized: "
Nov 8 11:44:42 trax dbmail/pop3d[29998]: Message:[serverchild]
serverchild.c,PerformChildTask(+349): incoming connection from [10.1.2.129]
by pid [29998]
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: <-- \001
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 500 5.5.1 Command
unrecognized: "\001"
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: --- 421 4.4.1
trax.tryx.org Lost input channel from file.tryx.org [10.1.2.129]
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: lost input channel from
file.tryx.org [10.1.2.129] to MSA after startup
Nov 8 11:44:42 trax sendmail[7596]: nA8JigNd007596: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax sendmail[7597]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7597]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: --- 421 4.4.1
trax.tryx.org Lost input channel from file.tryx.org [10.1.2.129]
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: lost input channel from
file.tryx.org [10.1.2.129] to MSA after startup
Nov 8 11:44:42 trax sendmail[7597]: nA8JigcP007597: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax dbmail/pop3d[29998]: Message:[pop3] pop3.c,pop3(+440):
user cjm logged in [messages=0, octets=0]
Nov 8 11:44:42 trax sendmail[7598]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7598]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: <-- EHLO File
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-trax.tryx.org
Hello file.tryx.org [10.1.2.129], pleased to meet you
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: ---
250-ENHANCEDSTATUSCODES
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-PIPELINING
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-8BITMIME
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-SIZE
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-DSN
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-AUTH DIGEST-MD5
NTLM CRAM-MD5 KERBEROS_V4 GSSAPI
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-STARTTLS
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250-DELIVERBY
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 250 HELP
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: <-- STARTTLS
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: --- 220 2.0.0 Ready to
start TLS
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, info: fds=9/3, err=5
Nov 8 11:44:42 trax sendmail[7598]: STARTTLS=server, error: accept
failed=0, SSL_error=5, errno=0, retry=-1
Nov 8 11:44:42 trax sendmail[7598]: nA8Jigh1007598: file.tryx.org
[10.1.2.129] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA
Nov 8 11:44:42 trax sendmail[7599]: NOQUEUE: connect from file.tryx.org
[10.1.2.129]
Nov 8 11:44:42 trax sendmail[7599]: AUTH: available mech=GSSAPI KERBEROS_V4
CRAM-MD5 NTLM DIGEST-MD5 ANONYMOUS, allowed mech=EXTERNAL DIGEST-MD5 NTLM
PLAIN CRAM-MD5 KERBEROS_V4 LOGIN GSSAPI
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: Milter: no active
filter
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 220 trax.tryx.org
ESMTP Sendmail; Sun, 8 Nov 2009 11:44:42 -0800
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- EHLO File
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-trax.tryx.org
Hello file.tryx.org [10.1.2.129], pleased to meet you
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: ---
250-ENHANCEDSTATUSCODES
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-PIPELINING
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-8BITMIME
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-SIZE
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DSN
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-AUTH DIGEST-MD5
NTLM CRAM-MD5 KERBEROS_V4 GSSAPI
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-STARTTLS
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250-DELIVERBY
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 250 HELP
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: <-- MAIL FROM:
<[email protected]>
Nov 8 11:44:42 trax sendmail[7599]: nA8JigDl007599: --- 530 5.7.0
Authentication required
Nov 8 11:44:42 trax dbmail/pop3d[29998]: Message:[pop3]
pop3.c,pop3_handle_connection(+188): user cjm logging out [messages=0,
octets=0]
Nov 8 11:44:59 trax sendmail[7599]: nA8JigDl007599: --- 421 4.4.1
trax.tryx.org Lost input channel from file.tryx.org [10.1.2.129]
Nov 8 11:44:59 trax sendmail[7599]: nA8JigDl007599: lost input channel from
file.tryx.org [10.1.2.129] to MSA after mail
 
I have removed the requirement for encryption to expose the authentication
problem. Please notice that Outlook reports:

2009.11.08 14:04:32 SMTP (smtp.tryx.org): Authorizing to server
2009.11.08 14:04:32 SMTP (smtp.tryx.org): Authorized to host


And sendmail reports:

Nov 8 14:11:10 trax sendmail[10829]: nA8MBAgg010829: <-- MAIL FROM:
<[email protected]>
Nov 8 14:11:10 trax sendmail[10829]: nA8MBAgg010829: --- 530 5.7.0
Authentication required


And I get a pop-up window from Outlook reporting:

Task '(e-mail address removed) - Sending' reported error (0x800CCC78) : 'Unable to send
the
message. Please verufy the e-mail address in your account properties. The
server
responded: 530 5.7.0 Authentication required'
 
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