There are no way in standard user interface for IIS (7.5) to map two Virtual Web Sites to SSL. The user interface only support assigned one Web Site to SSL.
To fix this, short version:
- Buy a wildcard certificate, *.mydomain.com
- Install certificate on web server and UAG (in my case)
- Assign one the SharePoint web site to https using the default user interface for IIS
- For the other(s) start command line in %windir%\system32\inetserv\
- appcmd list site (to list existing binding - for you information)
- appcmd set site /site.name:"MySite Host" /+bindings.[protocol='https',bindingInformation='*:443:mysite.mydomain.com']
- appcmd list site (to list existing binding - for you information)
- publish urls in UAG
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