On any of our websites running WordPress 2.3 the server gets stuck in an infinite redirection loop when using the https:// protocol.
https://truthmedia.com
https://sandbox3.wearetm.com
When disabling the canonical redirection it works fine.
Both are hosted on MediaTemple?, I do not know what type of server they are running, or what redirects they are using, so I cannot tell you what is conflicting.
I have opened a support request asking if they can give me any more info on what is happening behind the scenes.
(If you check and https://truthmedia.com seems to work, that is because I have disabled the canonical redirection, I will leave https://sandbox3.wearetm.com as is for testing though)