The COVID-19 pandemic accelerated technological advancements in education. However, when the threat of COVID-19 subsided some schools discontinued the use of technology-enhanced flipped classroom. This study reports on challenges that could have influenced the discontinued utilisation of technology-mediated flipped classroom model that supported some of the underprivileged high schools of South Africa during the COVID-19 era. While acknowledging that the final decision on whether to discontinue rests with the teachers, learner challenges are equally important as they can contribute to the teachers’ decisions. Hence, this study, anchored by the TPACK framework and Maslow’s hierarchy of needs theory, explored both learner and teacher challenges that influence discontinuation of the use of the flipped learning model. This entailed using semi-structured interviews of purposively selected teachers and learners (N=8) to close this gap in the literature on the use of flipped classroom in the post-COVID-19 era focusing on organic chemistry. Using deductive thematic analysis, the key challenges that could have contributed to the discontinuation of the use of this teaching model were identified as lack of access to Internet services, stable Wi-Fi and ability to navigate the online learning system, competence, motivation, effect of lack of support from the educational institutions and teacher overloading. These findings contribute to the literature on the continued use of this teaching model beyond emergencies such as COVID-19 by highlighting challenges that educational practitioners should be wary of. Additionally, the study has implications for the need to fast-track infrastructure and teacher professional development in underprivileged high schools.