Emergency remote instruction during the COVID-19 pandemic had an array of implications for youth and their families. This qualitative case study explored youth experiences and their parents’ perceptions about youth mental health and learning during imposed emergency remote instruction throughout the COVID-19 pandemic. Using a multi-informant and semi-longitudinal case study research design, the purpose of the study was to describe the resilience processes related to navigating remote learning at two different points in time (May 2020 and May 2021). Participants included four youth aged 12-17 years old and their four parents that totaled 16 separate semi-structured interviews. The findings include rich descriptions about the in-depth experiences of youth and their families navigating the uncharted territory during the pandemic with social restrictions and online learning living in Manitoba. Participants described themes related to learning, mental health, family dynamics, interpersonal competencies, and adaptive processes. These findings highlight the many systems and adaptive capacities within the youth, in relationships with caregivers, families, educators, helpers and friends, and in resources and capacities in order to support resilience in a post pandemic world. Many of these center around the powerful adaptive systems variously referred to as agency or mastery motivation, active coping, hope or optimism, and connection. The results have important implications for research and practice regarding resilience, education, and counselling.