The novel Coronavirus disease (COVID-10) which was declared a pandemic in March 2020 has disrupted learning programmes that rely extensively on work-integrated learning (WIL). This article reflects on the use of the 2016 online reverse video challenge as a remote learning alternative to WIL in the technical theatre stream of the Diploma in Performing Arts at the Tshwane University of Technology (TUT). A reversed intention practice-based assessment (or reverse video assessment) project was designed for the students to approximate the skills required for theatre technicians. This article is a conceptual exploration of the reverse video assessment design that involved exploring trends in reverse footage on online platforms and the professional practice of renowned South African artist and theatre maker, William Kentridge. The needs of contemporary South African students to be “tech-savvy” while faced with limited resources, was aligned with the requirements of the embedded simulated WIL curriculum. The reverse video assessment adopted a design research approach through the lens of play theory to conceptualise the edutainment approach to learning to relieve student anxiety during the pandemic. The assessment focused on three stages of development, namely, abstract thinking, three-dimensional object manipulation, and sequential organisation, which collectively result in a pragmatic creative process. The article will contribute to the remote learning body of knowledge which has come under greater focus during the pandemic. The ongoing pandemic necessitates a remote learning alternative to WIL to ensure continued learning without risking the health of students. The flexible nature of the reverse video assessment allows for the application thereof to different fields and levels of study