Constructionism suggests that people learn particularly well when they are creating personally meaningful artifacts for an audience. Design-oriented construction kits can provide affordances for creative, open-ended exploration and creation, but their use can be difficult to incorporate in a classroom setting where many learners are working at different rates or may find certain aspects of the activities more or less compelling. During the shared time in the classroom, what can be done to help students and instructors maintain awareness of opportunities for reflection, collaboration, or sharing? Once the shared time has passed, how can teachers and students review the work that was accomplished for reflection, assessment, or further exploration? What kinds of guidance might be useful for helping align student activities with the goals of the instructor? DigiQuilt is a constructionist toolkit for exploring math concepts through the creation of patchwork quilt blocks that solve mathematical challenges. In this presentation, we describe previous and ongoing work that aims to improve DigiQuilt in ways that support its reflective, meaningful use by teachers and learners in a classroom setting.