I am working on transitioning from an exchange 2007 server to an exchange 2013 server and have routed email to the new server by changing my asa port forwarding to the new ip address.
However during this transition process I need outside access to the old legacy server also for OWA. Thus I need port 443 to be able to forward to both the old exchange and the new exchange server as the owa process currently is going to the new server and it is passing it on to the legacy server when the mailbox is on the old server.
This process works perfectly fine inside the network but from the outside the legacy server can not be seen.
I added the 443 rules again for the legacy server and got a warning in the nat rules about overlapping.
Bottom line is it still does not work from the outside but works fine from the inside.
So how to a get a Cisco ASA 5505 to be able to pass 443 traffic based on server name etc.
You can't. what you need is a box able to direct traffic based on some arbitrary content (SNI might work) and an ASA isn't anywhere near advanced enough to do that. You are more probably looking at some
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