Here is my situation:
DNN version 4.05. SQL Server 2005. Windows Server 2005.
We have a single DNN install that we would like to load balance. We are using 4 machines: 2 IIS machines and a separate box for SQL Server and a FileShare for all of the DNN files. The 2 IIS machines are pointed at the file share so that we only need to keep one copy of DNN up to date.
Outside of that, we have a Coyote Point Load Balancer that takes care of incoming traffic on our URL.
So far, so good...

Now we need to add SSL into the mix and would like to use a single SSL cert on the load balancer (we've done this before with other non-DNN sites). Consequently, we would like to set up a couple of ports - 444 for normal traffic and 555 to handle SSL traffic. I've added appropriate entries into the Alias table.

When we try to look at the site now from a non-standard port, we get a page not found error. If I move the XX.XX.XX.XX:444 or :555 to the top of the alias list, the site resolves, but it resolves to the IP address instead of the URL. If I put the URL at the top of the alias list, it get s stuck in a redirect loop.

Anyone out there face this before?