@Greg OLone There are a few things that immediately come to mind:
- Are you sure that IIS isn't already binding to port 443?
- Are you sure that you have permission to bind to port 443? Have you tried another port (something above 1023) just to be sure?
- Is the filesystem case-sensitive? If so, the SSL certificate name must match the application exactly. SSLTest ≠ ssltest.crt
I'm curious... what do you mean by "re-keyed"?
1) IIS has only one "Default Site" in it and it is "stopped" by default so I dont think it would be binding to port 443.
2) I enabled the worker role to open 443 so that traffic can run through it. (firewall open)
To address 1 and 2 - Is there a way to see if the launched app indeed has an open listener to this port some how?
3) Cases match exactly.
~4) Re-keyed meant I generated a new Private key and a new CSR. I submitted this to godaddy using their "re-key" certificate option to overwrite the old key as an attempt to fix the problem. It did not, but I figured it was worth a shot at this point. I'm incredibly frustrated with trying to get Web Standalone working with SSL and I'm willing to try anything at this point. Next on the list is praying to the Juju Gods... *sigh