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.

"Chris Miller" Chris(a)InfoGreat.com wrote in message
...
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.

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:

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 - 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'