Multiple websites on one server

I'm going to distinguish the web browser (client), the web server, and the DNS server here, and will treat these as running on three separate computers. You might have one or more of those co-located on one box, adjust these references to your configuration as necessary.

The DNS translations are applicable only on the client; on the host box that is running with the web browser. The web server doesn't care about the DNS translation. The client needs the DNS to get the IP address of the web server, and it's off to the races from there.

Again, DNS translations are not relevant the web server. The particular web server that gets selected (Apache Virtual Host, what Apple calls a "Site") based on some information that is passed within the http (don't start working with https quite yet) connection from the web browser into the web server.

As for your DNS question, you'll probably want a CNAME (alias) entered in DNS database for the virtual hosts, even if you're awash with IP addresses. That alias must then match the name of the web server "Site". For testing, you can enter what amounts to CNAMES into /etc/hosts on the client, depending on your local set-up and your DNS server.

By default, the connections to all virtual hosts are via port 80. Stay there for now.

The web server selections are sensitive to the order of the "Sites" in the listing in Server Admin, too; you'll want the wildcard site (if you have that) at the end of the list.

Here are some of the basics: [Apache Tips: One Web Server, Multiple Distinct Web Sites|http://labs.hoffmanlabs.com/node/1282]. Comments on that are welcome.

In addition to what MrHoffman says, make sure that you don't have a wildcard (*) set in the Site Aliases section of your first web site. If you do then Apache will use this site's configuration for all sites, ignoring any other virtual hosts you have running on the same server.

You don't actually say what your failure state is (i.e. site not found? site1 always being served, regardless of hostname?, something else?) so it's hard to tell if that's the problem, but historically that's been the #1 cause of multiple sites not working in Mac OS X Server.

It would be typical to have one DNS zone for each domain or subdomain you're working with, and one A record for the server and multiple CNAMEs for the aliases, either in the same zone or (if you're serving up multiple domains) in the appropriate zone for the domain.

Also ensure the web browser client box is set up to use the DNS server.

This also presumes this configuration is entirely within the LAN, and that you're not trying to use the Mac OS X Server box as a firewall.

If you're mucking around with the zone stuff, set the Time To Live (TTL) value to a short interval, while you're messing with it. Otherwise expect to be flushing the DNS cache on the client.

What should the destination of the CNAME be set to? I've currently got it set to FQDN of the DNS name of the server itself.

You'd have, say, "MyServerAlias" within, say, the "example.com" zone (if you're not running an FQDN here) which would be "MyServerAlias.example.com" translating on the client box to, say, "myrealserver.example.net." (FQDN) for the CNAME, which then gets translated to the IP address, and whatever is in the URL bar sent over the network to the Apache Server via http.