Adolescents as a group of individuals are often overlooked in health related discussions, despite the need to tackle the health challenges they face during a crucial period of transition from childhood to adulthood. The various aspects of their health and well-being (psychological, social, developmental, and sexual) are impacted by a myriad of factors such as technology, poverty and, most recently, the COVID-19 pandemic. With a view to discussing these important issues and exploring some of the different aspects they impinge on, the SingHealth Duke-NUS Global Health Institute (SDGHI) and United Nations Population Fund (UNFPA) Lao PDR collaborated to organise a 4–part webinar series. The 4 webinars highlighted the key challenges and approaches in adolescent health and well-being in the region by: 1) looking at the impact of COVID-19 on adolescents, 2) understanding the implications of the rapidly evolving digital environment on their health, 3) examining the key approaches to sexual and reproductive health, 4) looking at poverty as an underlying determinant that increases the vulnerability and health risks of this demographic. It brought together speakers working in different areas of adolescent health and development from various countries in the region and provided a holistic picture of how the different aspects explored intersect and influence the overall health and well-being of adolescents.