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I know from previous experience that having servers in DMZ 1 accessing the public NATed IPs of servers in DMZ 2 on the same ASA (aka "hairpinning") is a tricky business in a single-context ASA. But is this still an issue with a multi-context firewall?

We currently have a physical web server that will be virtualised onto the same firewall as some (but not all) of its users, in a different DMZ. This would normally cause issues, as above, and DNS re-writing isn't an option, as not all of the web services have DNS names. With multi-context, and the web server in its own context with a shared internet interface, is that enough separation that my request packets make it all the way outside before hitting the external NAT address?

This is with 8.3.x software.

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The answer was, yes, it is enough separation. From the point of view of DMZ 1, the DMZ 2 device is outside.

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