This article describes the crossroads between learning analytics and learner engagement. The authors do this by describing specific challenges of using analytics to support student engagement from three distinct perspectives: pedagogical considerations, technological issues, and interface design concerns. While engaging online learners presents a major challenge to the educational community, the affordances of online learning environments and new advances in data analytics present many opportunities that can lead to improvements in our ability to fully engage students. The authors' work specifically underscores the fact that no single tool or system will be able to address all of the challenges involved. As a result, tools and content need to be open, interoperable, and modular. The important field of learning analytics will develop much more quickly when tools and work are shared across organizations and projects.