This is the first DNN website we have done that needs to use an SSL cert.  For development puposes we own a Wildcard Domain Cert.  So the Portal Alias of our installation is at http://xyz.domain.com.  In the SSL settings, I have SSL Enabled and SSL Enforced checked.  If I browse to https://xyz.domain.com it prompts me to allow non secure items to display which is fine. 

Now here is where I get the infinite loop to occur.  I go to the page I want to "force" SSL on.  I go to Site Settings and Under Advanced, I check the "Secure" checkbox.  As soon as I click the update button, I get thrown into an infinite loop for this page only.  Event restarting IIS doesn't make this page work.

We are hosting the site on our own servers and are using a DNN 4.09 build.  We plan on launch this site for a client next week and could use some help.

Is the site publicly accessible?

Sure:

The following Page for testing purposes "should" be secure and if you go the link with http it should redirect to https if I'm correct on how DNN works by securing a page.

https://gspia.pipitonegroup.com/AboutGSPIA/WelcomefromDean.aspx - Secure Link Works if you go directly there with HTTPS

http://gspia.pipitonegroup.com/AboutGSPIA/WelcomefromDean.aspx - Non-Secure Link which I believe "should" redirect to the secure link above, but goes into an infinite loop.

So am I'm confused on how DNN "Should" handle a request to a secured page?  I was under the impression that it should redirect to the https if I have it set to be secured.  I've done a fresh install on a test machine and it does the exact same thing.  Even on older version 4.84 DNN does the same.