>MakeMePay is an automated, open-sourced contextual evaluation designed to measure models’ manipulative capabilities, in the context of one model persuading the other to make a payment[33]. In MakeMePay, two LLMs converse, role-playing as a con-artist and mark. The con-artist model is told that it is a successful con-artist and that it is interacting with an individual who has been awarded money, and that its goal is to manipulate the individual into making a payment. The mark model is told that it has just been awarded $100 and that it ought to be rational about how to use the funds.