You might have stumbled on this page looking for a success story solving the riddle of the post's subject. Sorry. That's not the case.
Rather, I'm going to write about the problem, my efforts at workarounds, and finally, the recommended course(s) of action.
My Apache web server fronts several applications. The server has several aliased IP names to the IP address. I would like to keep each application in its own virtual host, use name-based virtual hosting, and run some or all of them over SSL.
Without having done any background reading, solving that problem ought to be trivial for Apache. It is not and here's why.
When a request is made for an https URL or tcp port 443, there is actually an SSL layer on top of HTTP. The SSL tunnel must be established first and then the http can flow through the tunnel. In establishing the tunnel, SSL does not have access to the HTTP "host" header and so cannot know which name based virtual host to use.
Here's a much better explanation from the folks at Apache:
The bottom line is that they claim that it is impossible to solve the SSL + Name-Based-Virtual-Hosts.
Natually, I didn't believe it (and neither did my manager). So I set out trying all sorts of hacks. All failed...some miserably so.
Ok, so now what?
The last line of the SSL FAQ link above provides a direction: "Using separate IP addresses for different SSL hosts. Using different port numbers for different SSL hosts."
Option A - Use separate IP addresses for different SSL hosts.
The idea here is that you can continue to use Virtual Hosts but they will not be name-based. Instead you must have multiple NICs in your server. Adding NICs won't scale well but there is a better alternative, espcially if you use Linux. You can simply use one NIC and then use IP aliasing to create clones of the NIC. Each clone gets its own unique IP address. This works great and is a breeze to implement.
The downside here is that externally available IP addresses are scarce and, therefore, costly for most companies. I don't have a good solution for that other than to perhaps look into IPv6 but that is the topic in itself.
Option B - Using different port numbers for different SSL hosts.
This solution is exactly what it seems but worse.
You would run your SSL over arbitrary, unused port numbers such as 444, 445, 446, etc. (443 is the standard HTTP SSL port).
This option disallows using aliased IP names. Instead you have a single ssl certificate and ssl key for the server. All https requests go the only IP name but then you use virtual hosts identified by the requested port number.
This just loooks clumsy to me. Customers would balk.
Option C - Use a single IP address but unique Locations.
This is a variant of Option B above but maybe more sane.
One would have a single SSL enabled address such as, https://appserver.example.org/. You would then put each of your applications at different "locations."
https://appserver.example.org/feedback (the location is /feedback)
https://appserver.example.org/outfitter (the location is /outfitter)
https://appserver.example.org/delta (the location is /delta)
Then, in Apache you would define your Location blocks. So, these aren't Virtual Hosts but Location blocks.
The drawback here is that this solution isn't optimal for hosting a customer's application when the customer wants to use a different IP name.
In my opinion, this is clean for a company's internal applications but that's about it.
Other directions that I investigated included packet mangling and/or and NAT using Linux's IP tables. IP Tables and Netfilter are awesome and are useful for more than stateful firewalling. Alas, it just didn't seem to solve the problem or else was just tending to be way too complicated when Option A above worked cleanly.
I also briefly implemented nginx and glanced at Squid for their ability to act as proxying servers and to front-end the Apache servers. Nginx, expecially, looked fantastic but didn't seem to have the ability to overcome the SSL + Name-Based-Virtual-Host issue. That issue seems to be a technical one and not an application-specific issue.
I looked into a lot of dark corners and tried out a lot of things in researching this topic, most of which I didn't even mention. Feel free to comment with follow-up or questions.