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I'm using SelfSSL7 to create a self signed certificate in IIS 7.5(Win Server 2K8 R2). I have 2 sites in IIS ( the default site and a test site). I ran the following to create the cert.

SelfSSL7.exe /Q /T /I "Default Web Site" /N cn=MyMachineName;cn=localhost /K 1024 /V 18250 SelfSSL7.exe /Q /T /I /S "TestSite" /N cn=myhostheader;cn=myhostheader.mydomain.com /K 1024 /V 18250 appcmd.exe set site /site.name:TestSite /bindings.[protocol='https',bindingInformation=':443:'].bindingInformation::443:myhostheader

This works but the https 443 binding for the "Default Site" ends up using the same certificate as the test site so I'm unable to use SSL for both sites on port 443. This article explains the issue but I can't seem to find a workaround. I would like to use a different self signed certs for SSL per website. How can I achieve this?

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This is not possible.

The TechNet forum post you linked involves trying to set up multiple sites on the same wildcard certificate on the same port, which is definitely possible.

However, using two distinct, different certificates on the same port as you are attempting falls into the realm of requiring TLS Server Name Indication. No current version of IIS supports this.

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  • What are my options? Should I generate just one certificate with the CN set to "*.domainname.com"(if this is possible) and use that for all web sites? May 22, 2011 at 5:59
  • Yes, that would work. May 22, 2011 at 6:16
  • Would the URLs for the sites need to be domain qualified. i.e if my host header is "mytestapp" then would the URL need to be mytestapp.mydomain.com. That is just mytestapp would not work? May 22, 2011 at 6:59
  • Wilcarding the CN does not work:I tried this: SelfSSL7 /Q /T /I "Default WebSite" /N cn=" *.mydomain.com";cn=mymachinename;cn=localhost /K 1024 /V 18250 This is the error I get:Common name (/N cn= *.mydomain.com) contains invalid characters. May 22, 2011 at 17:26
  • This is now supported since Version 8 in 2012 Jun 23, 2017 at 20:09

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