In our conceptional contribution to the journal “Group. Interaction. Organization.” (GIO), we analyze how telework affects informal workplace learning. Dynamic changes in the world of work require employees to continually adapt, and informal workplace learning is presumed to be an effective tool to cope with new demands. The accelerating use of information and communication technologies and the COVID-19 pandemic have led to an increase in telework. We integrate research findings to illustrate a modified learning infrastructure and develop propositions referring to the octagon model of informal workplace learning (Decius et al. 2019). For this purpose, we present a conceptual framework that demonstrates why telework reduces opportunities for informal learning due to social processes and role boundaries and increases opportunities via higher self-regulation. Furthermore, we develop ideas how supervisors could support informal learning by organizing social exchange, providing learning cues and resources, and design telework arrangements. Finally, we present implications for practice and future research with suggestions for the adaption of the octagon model for digital working contexts.