Q: How do I install self-signed SSL certificates on two IIS 6 websites on the same server where both sites use port 443 and are configured with host headers?
A: Multiple SSL sites on a single IIS server using host headers. <- the answer.
Basically, use SelfSSL or SSLDiag to create a cert with CN=*.example.com, then just point the second site to that cert in the Directory Security tab. Also, configure secure server bindings using adsutil (found in c:\inetpub\adminscripts).
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