Outlook 2003 SMTP TLS fails on any port except 25 w/ Sendmail 8.12.11/8.12.10

[publicnews.microsoft.com]

Outlook doesn't seem to want to issue a STARTLS command on anything but port
25. Instead, it tries to do direct SSL without STARTTLS negotiation. This is
a serious problem because I can't use secure SMTP at T-Mobile hotspots and
hotels: they block encrypted traffic on port 25.

According to Q307772 , this issue was respolved in Outlook 2002. It isn't.

Outlook logs:

*****************************
Failed SSL negotiation on port 6025
*****************************
2004.05.28 11:20:35 (e-mail address removed): Synch operation started (flags
= 00000001)
2004.05.28 11:20:35 (e-mail address removed): UploadItems: 1 messages to send
2004.05.28 11:20:35 SMTP (secure-email.luxsci.com): Begin execution
2004.05.28 11:20:35 SMTP (secure-email.luxsci.com): Port: 6025, Secure: SSL,
SPA: no
2004.05.28 11:20:35 SMTP (secure-email.luxsci.com): Finding host
2004.05.28 11:20:35 SMTP (secure-email.luxsci.com): Securing connection
2004.05.28 11:20:35 SMTP (secure-email.luxsci.com): Disconnected from host
2004.05.28 11:23:35 SMTP (secure-email.luxsci.com): End execution
2004.05.28 11:23:35 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr
= 0x800ccc7d
2004.05.28 11:23:35 (e-mail address removed): Synch operation completed


*****************************
Successful TLS negotiation on port 25
*****************************
2004.05.28 11:42:09 (e-mail address removed): Synch operation started (flags
= 00000001)
2004.05.28 11:42:09 (e-mail address removed): UploadItems: 1 messages to send
2004.05.28 11:42:09 SMTP (secure-email.luxsci.com): Begin execution
2004.05.28 11:42:09 SMTP (secure-email.luxsci.com): Port: 25, Secure: TLS,
SPA: no
2004.05.28 11:42:09 SMTP (secure-email.luxsci.com): Finding host
2004.05.28 11:42:09 SMTP (secure-email.luxsci.com): Connected to host
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 220 rs6.luxsci.com
ESMTP Sendmail 8.12.11/8.12.10; Fri, 28 May 2004 10:42:10 -0500
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] EHLO johngalt
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-rs6.luxsci.com
Hello pool-151-200-13-21.res.east.verizon.net [151.200.13.21], pleased to
meet you
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx>
250-ENHANCEDSTATUSCODES
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-PIPELINING
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-8BITMIME
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-SIZE 31457280
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-DSN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-ETRN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-AUTH LOGIN
PLAIN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-STARTTLS
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-DELIVERBY
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250 HELP
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Securing connection
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] STARTTLS
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 220 2.0.0 Ready to
start TLS
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Securing connection
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Connected to host
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] EHLO johngalt
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-rs6.luxsci.com
Hello pool-151-200-13-21.res.east.verizon.net [151.200.13.21], pleased to
meet you
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx>
250-ENHANCEDSTATUSCODES
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-PIPELINING
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-8BITMIME
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-SIZE 31457280
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-DSN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-ETRN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-AUTH LOGIN
PLAIN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250-DELIVERBY
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250 HELP
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Authorizing to server
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] AUTH LOGIN
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 334 VXNlcm5hbWU6
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx]
YnJlaXRlckB3b2xmZXJlaXRlci5jb20=
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 334 UGFzc3dvcmQ6
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] *****
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 235 2.0.0 OK
Authenticated
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Authorized to host
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): Connected to host
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] MAIL FROM: <*****>
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250 2.1.0
<*****>... Sender ok
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] RCPT TO: <*****>
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250 2.1.5
<*****>... Recipient ok
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] DATA
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 354 Enter mail, end
with "." on a line by itself
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): [tx] .
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): <rx> 250 2.0.0
i4SFgAAc021950 Message accepted for delivery
2004.05.28 11:42:10 SMTP (secure-email.luxsci.com): End execution
2004.05.28 11:42:10 (e-mail address removed): ReportStatus: RSF_COMPLETED, hr
= 0x00000000
2004.05.28 11:42:10 (e-mail address removed): Synch operation completed