Doubtfire is a web application that brings together an educational model based on constructive alignment and self-regulated learning to support students and educators. This model uses a task-oriented portfolio-based approach to assessment to scaffold and evidence different standards of achievement; backed by frequent formative feedback to support learning. Doubtfire’s technology not only draws together educational design principles, it further supports educators by minimising overheads associated with accessing and assessing student work and provides visualisations to monitor student progress. This chapter describes Doubtfire’s underpinning educational model and explores the experiences and advantages associated with teaching using this model and associated software.