This chapter examines the challenges and benefits of using reflection in ePortfolios, and reviews strategies for teaching and encouraging deep reflection. It includes a brief history of the use of reflection in portfolios, summaries of the main types of reflection, and general approaches for the development of student reflection. Barriers to successful reflection, such as inexperienced students and faculty, student fear and distrust of reflection, formulaic responses, and time constraints will be examined, and solutions will be proposed. The effects of the ePortfolio on reflection and the possibilities offered by technological advances and new software also will be reviewed. The chapter argues that faculty must carefully construct reflection learning objectives if they expect meaningful summative or formative assessment to take place. The author hopes that the discussion of prompts, scaffolding, cycling, and other mining techniques will help instructors transform reflection theory into practice.