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SSL certificate questions

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Sorry, but I have almost no experience with SSL certificates and how to implement them.

I have an IIS 8.5 server running on our intranet. We'll call it MYIISSERVER.

Under MYIISSERVER, I have several sites:

MYIISSERVER

     Sites

          Site1 - currently to access this site we use the address http://MYIISSERVER/Site1:8003

          Site2 - currently to access this site we use the address http://MYIISSERVER/Site2:8004

          Site3 - currently to access this site we use the address http://MYIISSERVER/Site3:8005

          Site4 - currently to access this site we use the address http://MYIISSERVER/Site4:8006

I now have to make all of these sites use SSL with the default HTTPS port of 443.

I have read about Server Name Indication(SNI) on IIS 8 and above. From what I understand, this is similar to using host header names on an unsecured site that uses port 80.

What is the best route to take on doing this? Do I get an individual certificate for each site? Do I get a SAN certificate to include all of the sites (if this is even possible for this scenario)?

Thanks,

rlynch106


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