This post is mostly a Note to self™ post for future reference.
Just had a classic "Unable to Start Debugging on the Web Server" error thrown in Visual Studio. This error can have like 50 different causes and it's always hard to figure out why it happend.
As usual you get an answer or at least a push in the right direction on Stack Overflow. It turns out that my recently added "global redirect from http to https" added via "UrlRewriter" module caused the error in this case.
The solution was simple and pretty obvious, i just changed my starting URL to https://my-dev-domain.com instead of http://my-dev-domain.com. As i said, pretty obvious but still a confusing error message.