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Is there a way to setup PFSense so that each VLAN get's a different DNS Host Override for the same domain.

As in, if I have 2 VLAN's and a client on each one goes to internalsite.com, it will redirect to different IP's based on the VLAN that they are in. Host override only lets me specify the host override for ALL or one VLAN not each one individually.

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Yes, it is possible. You can manually set your name server in your box. You have to connect to a same server that has a capability of deep packet inspection such that the DNS reply depends on the layer 2 ether VLAN field. It is unlikely that you will find such a name server unless configured by your ISP. So the solution is set up your own and send queries to that server. You might also want to clear the DNS cache in your browser or PC.

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