Plot hole: When they are on the subway train, they are talking about the worm and the virus. They said that everything would happen on the 14th. A couple of scenes later, when they are setting up for the traffic lights to go crazy at 9:00, Dade looks at his watch. You can see the date as 10-18, which is 4 days afterwards. (01:17:15 - 01:22:50)
Plot hole: If Dade is 18, like we find out at the beginning of the movie when his mom says happy birthday, then his probation is over (the judge said "until the time of your 18th birthday") and the terms restricting computer and phone usage no longer apply. The threats by Secret Service about violating his probation are BS since he's not on probation anymore.
Plot hole: To play a practical joke on Dade Murphy and other new students, they are told, "There's a pool on the roof." The victims accordingly go there and are trapped by the roof access door being one-way until – we don't see how or who frees them (Janitor? The least-mean of the prankers?). How do the new guys get onto the roof in the first place? I should think that the aforementioned access door would be locked to prevent it.
Suggested correction: Compared to half the mischief they cause, picking a lock is easy. I, myself, learned how to jimmy my middle school's door locks with my student ID and accordingly let myself in, and even did so in the sight of other students. It's only because I lacked their level of will for mayhem, their imagination for excuses, and, more importantly, their level of powerful parents to perform legal rescue, that I stopped doing so before the teachers got suspicious.
Suggested correction: This is in the form of a question. You can assume they lock the roof door, but they don't have to. Or, the person tricking them has unlocked the door for the prank. Or, they picked the lock. Plenty of possibilities, I'd say.