This article describes how online course features, email and cell phones were used to collect stories for a research study on learning persistence and success in online community college courses. This technology-based AI experience helped the field of online learning understand best practices for student retention, learning and success. It also showed that technology can be used to build relationships, gather reflections and share insights, and to develop the social construction of meaning. AI conversations helped build our knowledge of how online courses can be used for learning and transformation.