Background/Context: Portfolio assessment is a popular form of authentic assessment, but often portfolios become simply folders full of papers rather than student reflections on their work. Purpose/Objective/Research Question/Focus of Study: The author conducted a study aiming to help the ninth-grade students in his English language arts classroom be more reflective about their reading and writing portfolios. Research Design: This study was conducted as a teacher research study in two parts. The first part studied the effect on the reflectiveness of students when using a 10-minute one-on-one presentation with the teacher instead of a cover letter. From the data received from these first-semester presentations, the teacher-researcher categorized the students' statements into reflective and nonreflective categories. In the second part of the study, the teacher used these categories to teach students to speak more reflectively during their second-semester presentations. Conclusions/Recommendations: The author found that students can be taught to be more reflective about their work and that this newfound reflectiveness helps students take more control in their literacy education.