The rise of the platform era changes the way interactions are structured and enables transactions at a distance. The platform phenomena also enables co-creation of content, shifting the way services are delivered across diverse boundaries. This is especially apparent in workplaces, where the developments change roles, relationships and conditions for teaching and learning, creating the possibility of a two-sided market. From a socio-technical and socio-cultural learning perspective, this study primarily aims for a better understanding of platforms in higher educational settings. Using a learning platform as an illustrative case, we argue for platform context transactions that are not monetary transactions. The main contribution of the paper is to offer a discussion where we problematize the transactional concept in two-sided markets. The findings shed new light on emerging challenges and tensions in the interplay between the constant change of technology and what it means to work in such change. This has implications for both teaching and learning and offers insights that can be valuable for understanding the shift to online learning during the recent pandemic of covid-19.