Meditation has become a popular option to manage stress. Though studies examine technologies to assist in meditation, few explore how technology supports development of such skills for independent practice. From a two-phase mixed-methods study, we contribute learner-centered insights from 36 participants in a virtual reality environment designed to teach meditation skills to novices. In Phase I, we gathered affective and behavioral learner needs from 21 meditation novices, experts, and instructors to synthesize insights for learning. We then designed ZenVR: an interactive system to deliver an eight-lesson meditation curriculum to support learners’ progress. In Phase II, we conducted a 6-week longitudinal lab-based evaluation with 15 novice meditation learners. We found statistically significant improvements in mindfulness and self-reported meditation ability. Their insights from a self-managed practice, two weeks after the study ended, offered opportunities to understand how technology can be designed to offer progressive support without creating dependence in technology-mediated meditation practice.