Hi, Ray
Yes, when I log in I see the first page (the one you have on the left). If I click the button "Always use..." it takes me to the second page (the one you have on the right). If from that page I click to use HTTPS automatically that's when I get the error message (every time).
But if on the first page I click "Continute to Hotmail" or on the second page I click "Don't use HTTPS automatically" I am taken to my Inbox without any error message but with an HTTPS connection.
So, the SSL/HTTPS connection 'holds' throughout my webmail session, but I still have to choose it manually every time. It's not going directly/automatically to my Inbox from my login page. (I now click "continue to Hotmail" on the first page immediately.)
It's not a big deal, really. I'm glad they have finally implemented the more secure connection. (Yahoo, by contrast, is only now realizing how much their users want it since they're complaining about it being missing from the latest beta.) Still, I wish it wouldn't be so important to M$ to nickle-and-dime people with it: requiring a premium account for 'automatic' SSL (if that's what the 'account type' thing is all about) !