Pairing skilled workers with quality, high-paying jobs is one way to ensure Mississippi families succeed. However, limited access to skills training and low educational attainment keep many workers from securing good-paying skilled jobs. This gap between middle-skill positions and a comparably skilled workforce limits productivity for employers and access to jobs that support self-sufficiency for working families. Bridging the gap starts with investments in working families and skills training opportunities that are accessible for all Mississippians. This brief examines two enterprising programs tackling the intersections of persistent poverty, low educational attainment levels, and high unemployment rates, which threaten the economic security of Mississippians.