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If i have the A record in the dns pointed to a unique ip on our server, but have mutiple ip addresses associated with the host headers, will this cause an issue?

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You can't have multiple hosts using the same individual IP running SSL. Each one needing SSL must be unique.

You can however; 1. Have an SSL cert for www.site.com using IP 192.168.1.2 w/ host headers 2. Make a second host, www.company.com, using IP 192.168.1.2 w/ host headers. However this can not be assigned SSL using this IP.

Also, if you were to go to https:// www.company.com, you'd get a browser error about the certificate not matching https://www.site.com.

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you can SORT OF get around this by using alternate ports and rewrite rules (if they exist in IIS.) but yes, SSL encrypts the HTTP data, so the server does the SSL handshake before checking the HTTP header for the RequestURL. – neoice Oct 18 at 6:04
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I think you may have better luck on this question at http://www.serverfault.com

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