Although Affordance Theory has become increasingly influential in the Information Systems (IS) literature, the exact process through which the affordances of IT are actualised is less studied. In this paper, we build on a realist ontology of affordance and an interpretive epistemology of how affordances are perceived and actualised to trace the process of actualisation. On the basis of insights drawn from a case study of a telemedicine project in a remote mountainous region of Nepal, we develop a concept, which we call the “Trajectory of Affordances.” Trajectory of Affordances captures the complex relations between affordances of IT and the role of goal-oriented actors who perceive and then play a vital role in actualising them, using capabilities that are enabled by facilitating conditions to take the necessary action. Trajectory of Affordances shows that the affordances of IT can travel from perception to actualisation through multiple paths, sometimes clustering together, and in the process, often lead to the emergence of new affordances.