Resilience is defined as doing well despite significant hardships (Masten, 2014). Doing well, also known as demonstrating functional outcomes, implies that individuals unexpectedly illustrate positive development. Since very little is known about the long-term pathways of resilience in South African young people (Theron & Theron, 2010; Van Rensburg, Theron, & Rothmann, 2015), this project aimed to fill this gap. During the first phase (2015) of the study, 424 Grade 8 youths from eight Quintile 1 schools (no fee paying schools from disadvantaged communities) in the Sedibeng District, Gauteng province, South Africa participated. The researchers revisited these young people and followed up on how their resilience was/was not sustained in a second (2017) phase and third (2018) phase. Throughout the three phases, researchers were confronted with contextually unique difficulties such as over-exertion of staff and faculty as a resource, lack of infrastructure, insufficient communication (due to lack of funds) and accessing informed consents from participants (since legal guardians did not necessarily reside with learners) that hindered successful completion of second and third phases. We aim to explore these unique challenges and discuss possible strategies for longitudinal studies in the global South.