Mass incarceration and the associated statistics have become a growing concern worldwide; the burden of parental incarceration poses a significant risk to children and family members who are often left behind unattended. Children of imprisoned parents have continued to suffer the impact of not having a parental figure in their lives. This has created profound psychosocial challenges during and after their parent’s imprisonment. Whereas numerous studies have examined the existing outcomes of the same, limited studies have concentrated on understanding the outcomes from children, caretakers, ex-inmates, and social workers' perspectives comparatively to understanding coping strategies and expressed needs of children and affected families. This study hypothesizes that parental imprisonment is a predictor for family disruption, externalization, and internalization of deviant behaviour among children, leading to poor academic performance and dropouts for schooling children and increasing the risk of poverty within the affected families. This study used semi structured interviews and included data from a total participant sample (n=21), comprised of social workers (n=8), young people ages 17-24 years (n=5), caretakers (n=3), and ex-inmates (n=5). The study sought to compare life before and after separation among children and families of incarcerated parents over time. The results infer high risks for behaviour internalization, antisocial–delinquencies, school disruption, dropout, lowered academic performance, family economic decline and strain, and relationship disruption outcomes reported from all four categories of respondents. That said, this has created both positive and maladaptive coping strategies, with some children reporting resorting to fellow peers, friends, sports, child hard labour, prayers, and other theft, drugs and alcohol use in dealing with the post traumatic stress disorders, and caretakers, and ex-inmates resorting to seeking assistance within their extended families ties, obtaining business activities to improve their misfortunes that arose from the imprisonment of a primary giver in the family, these have resulted in some positive outcomes as well as negative implications. Conclusively, children and young people whose parents are in prison face significant vulnerabilities due to multiple risk factors that increase their likelihood of experiencing adverse outcomes. To avert and mitigate the above, participants called for increased educational support to children, social support assistance, guidance and counselling services, material support, and financial aid as a way forward and a means of providing lasting solutions to their challenges. The impact of parental incarceration on these children goes beyond the typical effects of separation, custodial solutions, and associated risks.