Recent changes to federal Medicaid policy have afforded states new flexibilities to improve access to and continuity of healthcare services for individuals as they reenter the community post-incarceration. This white paper discusses several reasons why states may pursue these authorities and offers considerations for waiver design and implementation. We provide readers with background on why a reentry 1115 waiver can be impactful for justice-involved populations and provide a framework for states to approach program design and implementation through a series of three distinct phases.