Uber and Lyft’s business model has long depended on treating drivers as independent contractors, a classification that typically means no guaranteed minimum wage, paid leave, or employer-provided benefits. In Massachusetts, that model collided with strict worker-protection laws and an active enforcement posture: the state attorney general sued in 2020 alleging that, despite the companies’ control over key aspects of work through their apps, drivers were effectively performing employee-like labor while missing legal safeguards. The case covered people who drove in Massachusetts between July 14, 2020, and July 2, 2024, and the settlement sets up automatic payments (no claim form required) largely based on miles driven and how far a driver’s net pay fell below the minimum wage after expenses. The $175 million settlement matters because it does more than pay back alleged wage shortfalls—it reshapes rules for ongoing gig work in the state. Alongside restitution (with separate minimum allocations for Uber and Lyft drivers), the agreement creates a minimum earnings floor for “engaged time,” paid sick leave accrual, a stipend to participate in the state’s paid family and medical leave program, access to pooled health coverage for qualifying drivers, company-paid occupational accident insurance, and due-process style protections like clearer pay transparency and a deactivation appeals process. The lawsuit’s significance is also regulatory: it presses the question at the heart of many gig-economy fights—when app-based workers should be treated as employees under state wage-and-hour standards versus contractors—and it shows how states can use enforcement and settlement terms to set de facto labor standards even without reclassifying everyone as employees. More broadly, the Massachusetts resolution fits into a national pattern of misclassification and wage claims against gig platforms, echoing disputes in other states where regulators and courts have scrutinized minimum wage compliance, expense reimbursement, retaliation protections, and access to benefits for app-based workers. Similar battles have played out around “ABC test” style standards and ballot-initiative carveouts, underscoring that the legal landscape is fragmented: some jurisdictions push toward employee status, while others experiment with hybrid benefit floors tied to measurable work time. For the ride-hailing industry, the deal signals that even absent a definitive nationwide rule, state-by-state settlements can effectively impose earnings guarantees, leave policies, insurance coverage, and transparency requirements that may become templates for future negotiations and litigation.