The role of reflection in the learning process has taken on new significance in a digital environment. The potential of using innovative teaching methods to prompt first-year writing students to self-regulate learning behaviors and write more critical reflection statements when using electronic portfolios was studied over eight fall semesters. Results showed that using student surveys and focused in-class discussion in conjunction with consistent ePortfolio assignments not only dramatically increased the length of reflection statements written but also the depth of thinking shown in those statements. These results demonstrate the effectiveness of using intentional instructional strategies for helping students develop self-regulation and critical reflection skills.