Most people who are incarcerated in the US are parents, yet little is known about the context and experiences of family connection when a parent is incarcerated. This study aims to provide family perspectives and experiences during a parent’s incarceration for providers and organizations to consider when supporting children who have incarcerated parent(s) and their families throughout incarceration. From March to August 2020, we recruited adolescents (12–18 years) who have or had a parent incarcerated, caregivers of children of incarcerated parents, and parents upon one year of release. Families were recruited by emailing flyers to community-based organizations and schools using convenience-based and snowball recruitment methods. Participants were interviewed using a semi-structured interview guide. We interviewed 26 participants: 10 youth, 6 parents released from incarceration in the last year, and 10 caregivers, who mainly resided in the state of Ohio. Three themes emerged during the incarceration phase: the high cost of parental incarceration (financial, emotional, and visiting), barriers to connection (intimidating and strict process, physical barriers, quality of phone calls), and family resource suggestions (age and developmental communication resources, community-based supports, stigma reduction). Families primarily discussed these themes along with the need for additional individual and community-based supports. Findings relay the importance of family-centered interventions during incarceration to reduce barriers to staying connected. We discuss families’ suggestions on supportive services to help the family unit access resources and improve communication during incarceration, to better support the next phase of transition, reintegrating back into society.