There’s a mad dash to automate the world’s most hated calls. Have an unpaid bill? You’ll hear from an AI debt collector sometime soon.

She introduced herself as Eve, but Ben knew right away that the voice on the other end of the line was a bot. Eve knew his name. She also knew how much money he’d owed a former landlord ($266). She didn’t seem to know that he’d settled with a collection agency five months prior. Eve said she was an AI agent from ProCollect and was calling to collect a debt. “Would you like to resolve it today by card or bank transfer?” she asked.

Ben had stepped outside on a balmy April afternoon in Portland, Oregon, to take the phone call. (He asked that WIRED use a pseudonym so he could speak freely about a financial issue.) As he stood in the sun, he wondered what he’d have to say to make Eve hand off a call to a human. “I figured it was just going to kick me over to a person when I asked about repayment structure or anything more technical,” he says. But Eve stayed on the line, so Ben did, too. He decided—why not?—to mess with the bot a little.

Ben says he asked the bot to engage in some role-play, in which he was “just a little guy” and his debt was like a giantess prone to trampling him. He wanted to see how weird Eve would get. The bot haltingly played along for a few minutes, he says, but then abruptly punted him to a call center employee. The human agent didn’t disclose whether they’d heard Ben’s bizarre conversation with the AI. They did, however, quickly clear up the confusion: “They looked me up in the system,” he recalls. “Found that the balance was zero.”

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