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Online technologies can facilitate new assessment designs, where students develop, analyse and reflect upon their learning. Online multi-stage assignments provide students with opportunities to submit and share their work over an extended period in social sharing spaces such as blogging and discussion forums. This study explores the challenges experienced by students while completing online multi-stage assignments and the processes of self-regulated learning students engaged with to overcome such challenges. We present interview data from three qualitative case studies involving 34 students across two Australian universities. The results show all students experienced challenges while working on multi-stage assignments. Students engaged with both online and offline social cues to regulate their learning and overcome task challenges. We discuss the design implications and provide recommendations for further research.