I found myself needing to create an Azure Hybrid connection from a web application hosted on Azure to a WebAPI application hosting on a server inside a company network. I kept running into one issue that was preventing me from successfully creating my connection. If you find, like me, that no matter what you try, your Hybrid connection just keeps telling you ‘Not Connected’, there’s one thing you should check in your installed Windows Features list.
“Visual Studio debugging – SSL Connection / Connection Reset with IISExpress – Stack Overflow
Sometimes it can be a huge pain in the rear to work with SSL on local IIS or IIS Express in Visual Studio. I was trying to debug an issue with my authentication flow and just could not get my auth server to run locally. I finally came across this StackOverflow answer and discovered that I was running into the issue where my port for IIS Express was something like 66234. I didn’t know that to get it to work right, you have set the port between 44300 and 44398. And like Jason’s answer, absolutely nothing I could see either during setup or runtime told me that.