Hi - it appears Outlook Connector (14.0.6123.5001 - latest download) is not using HTTPS when sending my MSN dot com Premium domain messages from Outlook 2007 on Vista (latest Windows updates installed for all).  I have the annual fee MSN account, if that's relevant for this issue.  And I've uninstalled and re-installed the latest Connector, but that had no effect.

When sending a test email to myself thru Outlook, the message header does not indicate any reference to TLS, SSL or HTTPS as I would have expected.

More importantly, a few months ago I used a public Wi-Fi without VPN for the first/only time, assuming that my Outlook/MSN email traffic would be secure, since the latest Connector supports HTTPS.  An hour later, I discovered my MSN account had been compromised and dozens of spam/phishing emails were found in my Sent Box.  The account was quickly re-secured, but that still indicates a hole in my Outlook/MSN email security.

The Outlook Tools/Account Settings for my MSN account do not explicitly indicate any security settings.  How can I definitiely confirm whether my messages are being properly sent via HTTPS thru Connector?

SSL is on by default in Outlook.com. It can't be turned off.