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I had some fun today attempting to set up multiple ssl enabled websites on OS X Server 10.4.  After about 5 hours of hacking away at the server admin app and the network preference panel, we almost gave up.  We nearly even dropped a nice $700 to get Apple involved (‘Enterprise’ incident my foot). 

It turns out that we had our terms mixed up.  The whole while, we had been trying to enable VLAN for the server, thinking that would allow us to handle multiple IP addresses coming into one NIC card.  We also assumed that IP aliases did the same thing as VLAN.  After some heavy Googling, we discovered that there is a quite a difference b/t the two.  IP aliasing is what we were looking for.  While I did this mainly through the command line (via ifconfig), there is also the way of the GUI: 

In the Network preference pane, add a new connection to the external network card.  Call it whatever you’d like, but manually set the address to whatever IP you’re attempting to alias. 
Then, set the subnet mask to ‘255.255.255.255’.  This should minimize chances of getting a duplicate address error as well as preventing you from having to set a route.

After doing so, we pinged the address (to emulate outside traffic) and it worked perfectly.  Although the instructions on this page were related to FreeBSD, I found it extremely helpful since OS X is BSD based.  

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