re: Spinoff: major plot holes in movies you've noticed

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They're constantly monitoring them for their own safety in case an agent should find them.

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I don't think this is even true. And if they are constantly monitoring them, they can't see everyone everywhere all the time. A couple times Tank is caught off guard by something and he had to switch screens to see different things.

I don't think it would've been that far fetched for Cypher to slip out for dinner.

Again, he could've just slipped into the Matrix under false pretenses, or given The Matrix the codes to the ships computer to block the signal while Cypher was there, etc...