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I have two sites:

I have two SSL certificates for each of the above domains.

When install certificate #2 for, it tells me:

At least one other site is using the same HTTPS binding and the binding is configured with a different certificate

Is it not possible in any way to install these two certificates on one server?!

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up vote 1 down vote accepted

You can't assign different SSL certificates to sites that are only differentiated by host headers. You would need to have the sites on separate IP addresses.

Another option is to setup a wildcard SSL certificate (which you could then apply to all sites hosted under * on the server.) There is a catch though - you still can't apply the certificate through the GUI. Instead you need to use a command line to apply the certificate.

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