I followed this tutorial for creating Signed SSL certificates on Windows for development purposes, and it worked great for one of my domains(I\'m using hosts file to simulat
As Rahul stated, it is a common Chrome and an OSX bug. I was having similar issues in the past. In fact I finally got tired of making the 2 [yes I know it is not many] additional clicks when testing a local site for work.
As for a possible workaround to this issue [using Windows], I would using one of the many self signing certificate utilities available.
Recommended Steps: