Stupidity: Harold isn't sure whether to trust the flash drive Claire gives him, worrying connecting it to his laptop will send Samaritan all his personal connections. Somehow it doesn't occur to him to just use a completely disconnected / airgapped laptop, in a Faraday cage or similar like the one he kept Root in. If the flash drive had malicious code on it, nothing could be transmitted anyway.
Continuity mistake: Reese orders the cab driver to smash through a car blocking their escape which causes considerable damage to the front driver's side of the car. This damage is shown in one of those computerized captured pictures this show uses throughout each episode. Then in the next scene, when the cabbie is standing alongside his now parked cab, the front driver's side is now perfect, but when he walks around the car to talk to Reese, the passenger side is damaged. The passenger side had been untouched in the crash.
Harold Finch: I'm a very private person.
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