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Is there such thing as a firewall with packet inspection? Most outbound firewalls simply prompt the user with "program.exe is trying to connect to the internet - allow or deny?". I find it impossible to make an informed decision without seeing the actual content being transmitted.

Ideally what I'd like is an outbound firewall that gives me a third option: "inspect packets" which kicks in a wireshark style monitor that lets me see what the application is trying to send and receive. This would allow me to pass packets one-by-one until I'm reasonably confident that the application is legitimate.

It would be great if such a firewall existed for Windows but I'd also be curious to hear if there's anything available on other OSes or in server environments too.

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You probably won't find it for desktop firewalls. That feature requires a much higher level of network knowledge than most users have/are willing to study.

Therefore, firewall companies won't put much effort developing something like this.

On the other hand, professional network appliances tend to be more inclined in that direction. I know that the Palo Alto Firewalls have some tools for capturing and analyzing traffic "wireshark style".

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