Navigating and maintaining enrollment in work related Medicaid buy-in programs is no easy task. Many state programs provide great incentives for certain types of disabilities and low income earners, but too often those with most severe disabilities and those looking to advance in a particular career find more disincentives than incentives. Strict resource and earned income limits force enrollees to choose between work and government benefits, with the latter needed to survive. Additionally, most state programs count spousal income which punishes enrollees for getting married and promotes non-marital relationships for maintaining vital benefits. Ideas and changes to strengthen Medicaid buy-in programs need to be shared so that stakeholders across the country can start pushing decision-makers to create real incentives that work.