Nearly 1 in every 14 youth have had a parent incarcerated at some point. In any given year, over 9 million adults from jail and 700,000 adults from prison return to their families and communities. However, few studies have explored the family experiences during re‐entry or have provided suggestions on how to best support children during this time. The goal of this qualitative study was to describe family experiences and provide their considerations on how to better support children during the period of parent's re‐entry. Qualitative data was gathered from 26 participants using semi‐structured, in‐depth phone interviews from March to August 2020. The sample included 10 youth (12–18 years) who have had a parent incarcerated, 10 custodial caregivers of youth who have had incarcerated parents, and 6 parents released from incarceration. Qualitative content analysis and open‐coding procedures were used to determine themes across raters. Experiences centred on the challenges of assimilating to new family roles upon the parent returning home and to the community. Families also shared the difficulty in navigating parole restrictions and managing fears surrounding the recidivism of the parent. Three primary themes were deduced as relationship‐building obstacles, unaligned family expectations and parole‐related family burdens. Results from this study revealed suggestions that may address youth, caregiver and returning parent's needs during the re‐entry phase. Family counselling and peer support groups may improve the process of mending or forming relationships. Access to re‐entry programs, mental health services, and parental education may better align family expectations. Transparent wrap‐around social services and decreasing legal challenges may reduce the parole‐related burdens on the family.