We have a test server that I'm trying to change over to HTTPS/SSL, and it has both an internal IP and an external IP. We have to use self-signed certificates for this particular server. There was one time in the past that I did some R&D on RTMPS with Flash, and so I still had a list of steps lying around to create a self-signed certificate for the internal IP, and to place it in the trusted store on client machines.
That being said, I need to get this working simultaneously for both the internal and external IPs. When I try to use the same steps to produce and trust a certificate for the external IP, the server keeps trying to fool around with the internal IP's certifcate, even when the client using the external IP. This apparently has something to do with it going through HTTP headers and getting the certificate for the default site. So even if the external IP's certificate is trusted, the client machine keeps generating a security warning when browsing to the site on the external IP.
Completely casting my previous notes on how to do this with the internal IP aside, how can this be handled simulatenously for both an internal and an external IP? How can you use self-signed certificates for both IPs, with neither generating a security warning in the client's browser?
Note that this is not a duplicate. I understand there's information out there about Subject Alternate Names, wildcard certificates, etc. However:
Much of it is for Apache; I'm using IIS 7.
Much of it is for Linux; I'm using Windows.
It also tends to deal with domain names, which seem to be necessary for wildcard certificates; I'm using IPs only.
Some of what's left at this point expects me to have options in IIS or in Windows that are not universally available.
What few pieces may be left are a little over my head, and the steps they use expect some pre-existing knowledge that's just not there. In other words, they skip steps, jump to advanced topics, etc.
What is a clear list of steps to get this done, assuming that the server is IIS 7 / Windows Server 2008 R2, and that the client machines are using Windows 7 (sometimes Windows Embedded Standard) and different versions of IE? The clients are accessing the pages, web services, and such through the IP addresses, and I have been using OpenSSL (though I'm open to other options). Thank you.