I have 2 projects, a Web API and a client angularJS project (that was created using the Empty Project template). My client has asked me to force SSL, so for the Web API I create
I had the same situation with 2 projects. Visual Studio 2015 correctly assigned differing URL port numbers for HTTP but mapped both projects to 44300 for HTTPS.
AFAIK the applicationhost.config in .vs\config seems to define the IIS Express environment and tell IIS Express how to behave when invoked. This information doesn't feedback into Visual Studio.
Visual Studio appears to rely on settings in the .csproj file. This is the SSL port value you see when you look at properties for the project in VS.
I was able untangle the two projects by adjusting both:
.csproj
true 44301
applicationhost.config
Update:
The file .csproj.user also has SSL Port configuration, to avoid the overwriting of the SSL port number in the applicationhost.config file, .csproj.user should be updated too.
true 44301