I went through this whole procedure
http://www.hanselman.com/blog/WorkingWithSSLAtDevelopmentTimeIsEasierWithIISExpress.aspx
a couple weeks ago and got https working on port 443 of all my IPs. The machine was rebooted a few days ago and I tried accessing the site again today (launched via VS2010, IIS express tray shows site running on 80 and 443). The http is working fine but https just says "internet explorer cannot display the page". I can see with netstat that the system process is listening on port 443 but I don't get anything in the browser. Fiddler shows some tunnel activity but nothing much else. What should I check to get this back up and running? All the steps on the above blog were voodoo to me so now that it's not working I don't really know where to start.
-JT
Did you try the following (posted at the bottom of http://www.hanselman.com/blog/WorkingWithSSLAtDevelopmentTimeIsEasierWithIISExpress.aspx).
"I think by moving the self signed cert from Personal to Trusted Root
CA directory causes a problem that SSL stops working after developers
reboot their machines. (Don't know how it happens, but it does happen
consistently.) I finally get around this issue by export and re-import
the self-signed cert into the trusted root directory (instead of
simply drag it over). Now my self-signed cert is considered and I
don't need to REINSTALL/REPAIR IIS Express every time I reboot the
machine. "
for me problem was with port number: my Visual Studio 2013/IIS Express configured app port number was NOT in the range :44300-:44398
full answer about same problem: https://stackoverflow.com/a/24957146/908936