This collaborative self-study centers on the experiences of four teacher educators facilitating preservice teacher learning in four separate community-based settings. Specifically, we examined the ways these community-based field experiences enhanced and challenged our work as teacher educators. We identified enhancements related to the settings, augmentation of preservice teacher learning, and collaboration with professionals in the field. The challenges we identified related to logistics working in community-based settings, including location, coordination with community professionals, and teaching in community-based settings. Findings across these settings and our four institutions compel us to advocate for teacher education programs to purposefully include community-based experiences as part of the preservice teachers' field experiences. Doing so can support and augment teacher educators' abilities to learn from teaching as well as challenge and extend preservice teachers' learning.