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I've always thought that the Gatekeeper's ledger told him what travel packages each soul had. Remember in the opening Year Four cutscene he's asking for each person's name, he consults the ledger, and intones "Waiting area two." The ledger says (I'm guessing) that someone has a ticket, that someone has not arrived on the train, and a red flag goes up in the Gatekeeper's head.
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