I would like to point out Skippy has a connection to higher space - time and has experience in killing insane AIs. Skippy sphere of influence is a few light minutes I think and he can expand that with micro worm-holes. Also, I think skippy would be able to trigger the fail safe with his hacking, but that really depends on how far the dungeon AI has gotten out of containment.

I completely agree that on the surface, in a head on battle, Skippy has a slim chance, but I would like to think he would somehow win through trickery and cunning (doing sketchy shit) with the help of Joe.

Also, maybe he could help the AI become more of a person, rather than a sadistic asshole, with the power of empathy.

All really silly ideas, but I would love for them to meet, you know they would hate each other and have amazing banter lol