Note: this will potentially solve the issue when Visual Studio shows the following error upon trying to debug: “Unable to debug the web server… An error occurred on a send.”
The problem can be solved by re-creating and adding a SSL cert to the port 443 binding of the default web application.
Follow the following steps:
From IIS, under the local server, open “Server Certificates”. Use an existing cert or create a self-signed cert, give it a name.
Select the Web application(not a virtual directory) that you want to use. Edit the bindings, add a binding for https port 443 and select the certificate you created previously and then save.
Note: when running applications off an existing web application in IIS, make sure to create virtual directories for each app if they are not available, you can do so by going to the project’s properties, under “Using local IIS server”, next to the URL of the app click the button “Create virtual directory”