We reflect on translating participatory and experiential learning methodologies into an online teaching environment through a Virtual Learning Environment (VLE) that simulates the "real-world" contexts of international development in order to develop an applied critical understanding of gender analysis and gender mainstreaming. Rather than being prescriptive, the paper aims to contribute to the growing body of literature that emphasizes the potential of using online technologies for providing opportunities for experiential and work-integrated learning. Our experience leads us to conclude that VLEs provide opportunities to facilitate knowledge contextualization and prepare students for an uncertain and complex world of work. (Contains 1 figure, 1 table, and 3 notes.)