I know this is a old thread and maybe no one is watching it anymore but I'm going to be dealing with a similar situation and trying to sort it out. All my past experience is with non-Cisco products so I a not familiar with ASA (yet). In the original question here I think it is complicated by having multiple private IPs on the *same* web server. This should not really be. Since it is one server it can do fine with multple sites all runing on the same port 80 and the same IP# as long as they are separated via Host Headers. If this were done then the question to me would be "Does the ASA retain the hostHeader when it passed the traffic back to the web server?" If the answer to that is "Yes" then the problem is solved. The ASA does not need to "care" about individual web sites,...all it has to do is take whatever comes in on the Public IP on port 80 and send it back the the Web server on port 80 at whatever Single IP# it is (should be) running and then the Web Server software "sorts it out" and picks the correct web site to feed it to. Would this be a correct way to look at it?
... View more