People on community supervision often face multiple barriers to accessing health care while also experiencing higher rates of chronic diseases, behavioral health conditions, and infectious diseases compared to the general population. Recent developments, including a Medicaid demonstration opportunity designed to improve care transitions for people in reentry, offer community supervision professionals more options for connecting people with needed care. To fully take advantage, community supervision agencies will need to partner with local health care providers that offer Medicaid-covered telehealth services for primary, behavioral, and specialty care. This guide outlines five practical steps community supervision leaders can take to engage health care providers and expand access to these services.