An $80 million fine and chatbot blunders hang over Block's push to automate financial recommendationsThat human-in-the-loop caution reflects a sensitivity that gains additional weight given Block's recent history. In January 2025, 48 state financial regulators imposed an $80 million fine on Block for violations of Bank Secrecy Act and anti-money laundering laws related to Cash App. The Connecticut Department of Banking stated in announcing the settlement that regulators "found Block was not in compliance with certain requirements, creating the potential that its services could be used to support money laundering, terrorism financing, or other illegal activities." The Illinois Department of Financial and Professional Regulation simultaneously joined the coordinated enforcement action.
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