I know this question is old, but for reference, if anyone wants an answer.
http://www.hanselman.com/blog/WorkingWithSSLAtDevelopmentTimeIsEasierWithIISExpress.aspx
I think the new IIS Express 8 can be configured in a similar way.
Edit: applicationHost.config for detailed configuration steps follow URL ^
<site name="MvcApplication18" id="39"> <application path="/" applicationPool="Clr4IntegratedAppPool"> <virtualDirectory path="/" physicalPath="c:\users\scottha\documents\visual studio 2010\Projects\MvcApplication18\MvcApplication18" /> </application> <bindings> <binding protocol="http" bindingInformation="*:15408:localhost" /> <binding protocol="https" bindingInformation="*:44302:localhost" /> <binding protocol="http" bindingInformation="*:80:hanselman-w500" /> <binding protocol="https" bindingInformation="*:443:hanselman-w500" /> </bindings> </site>
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