In my case, I created a self-signed certificate and had it working, except I was getting an error in the browser because the certificate was untrusted. So, I moved the cert into the Trusted Root Certification Authorities > Certificates folder in the Certificates snapin. It worked, and then I closed Visual Studio for the day.
The following day, I started my project and I received the error mentioned in the original question. The issue is that the certificate you configured IISExpress with must exist in the Personal > Certificates folder or HTTPS will stop working. Once IIS Express successfully starts, you can drag the cert back to the trusted location. It'll continue to work until you restart IIS Express.
Not wanting to fuss with dragging the cert back and forth every time, I just place a copy of the certificate in both places and now everything works fine.