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To monitor the outgoing and incoming packets on my ps4, I want to use fiddler. Fiddler works via an custom SSL certificate, but you can use an external device but that device also has to install the ssl certificate, so im asking here if its possible to install a custom ssl certificate on an ps4, jb on non jb doesnt matter.

You can't install custom SSL Certs on a PS4 running OFW. As for CFW, I'm not 100% positive.

If you're trying to simply see incoming and outgoing traffic you're best bet is to point the PS4 to the Fiddler proxy to see all HTTP interactions / connections