Work-related policies, including minimum wage and food assistance work requirements, can affect food security for people with lower incomes. This study conducted 112 qualitative interviews to understand participant policy experiences in two contexts (Raleigh, North Carolina and Minneapolis, Minnesota). Participants experienced frequent, destabilizing changes to their United States Department of Agriculture Supplemental Nutrition Assistance Program benefits, which they identified as part of a broader safety net. Raleigh workers described an unsupportive policy environment; Minneapolis workers reaped few benefits from an ongoing wage increase. Many workers face complex financial tradeoffs; more sophisticated evaluations should consider broader policy contexts and long-range effects.