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19:10
Looking for suggestions. I have a Windows 2016/IIS 10 box. I have two sites hosted. Each have separate external IP addresses and SSL certificates. Each site are bound to their respective IP address. When I try accessing either of them, I get the error "This site can't be reached." And regardless of external access, I should be able to access them internally. Not sure if this is a question worth posting on main or if it's a dumb mistake on my part.
Also, nothing in IIS logs, nothing in Event Viewer (that I could see). Not sure what's going on. This is the first time I've tried hosting two different sites on one server that didn't have code tightly coupled together.
 
1 hour later…
20:41
I got it working with someone's help. I needed to bind the server's internal IP address to each of the sites, and enable "Server Name Indication" on one of the sites.

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