Widely across the globe, COVID-19 has placed massive strain on various parameters of life, including child protection, health, education and economic systems. Apart from these visible threats, this situation is having an ongoing devastating impact on the mental health and psychological wellbeing of people. Most young people leaving child care institutions (CCIs) on turning 18 are generally not prepared to leave care, but the transition has become even more difficult and worrisome during the pandemic. During the lockdown, most of these young people were stuck in their CCIs, and their rehabilitation plans—if they were made—could not be implemented, even though there were several mandates around Aftercare, as prescribed in The Juvenile Justice Act, 2015. The Care Leavers faced difficulties in various life domains, including a lack of access to higher education, the loss of jobs, economic disruptions, and social isolation, along with an overall impact on their mental health and physical health as an aftermath of COVID-19. Based on these issues and years of experience as practitioners, Udayan Care—an NGO in India—started a programme named the Aftercare Outreach Program (AOP), supporting Aftercare youth (Care Leavers) in their transition process in order to make them job-ready. This is an exploratory study designed to collect and analyse the data collected from the Care Leavers supported by the Aftercare Outreach Program (AOP), which included 54 Care Leavers from two places enrolled in it, i.e., 42 Care Leavers from Delhi and 12 from Vadodara. The findings of the study clearly indicate that planned and supported transition like AOP intervention can make a difference in the lives of Care Leavers, and can help them towards independent living, even more so in unprecedented times like COVID-19.