How do you enable SSL for a project in Visual Studio 2017?
In VS15, I could select Project -> Properties -> Debug -> Enable SSL. This option is not available in VS20
Ports are locked down in IIS Express so that it doesn't have to be run as Administrator...
Valid Ports are 44300 - 44399
Check out the Dev Community article https://developercommunity.visualstudio.com/content/problem/39430/changing-port-number-in-a-web-project-does-not-imm.html
You can edit launchSettings.json, but the ssl ports must fall in this range.