Outlook 2003 and TLS

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...

Outlook 2003 and TLS