Mathematical modeling is a high-leverage topic; it is critical to students’ participation in STEM education and supports civic engagement. Until recently, research on modeling at the elementary level has been underemphasized, particularly research on supports and challenges for teachers who engage in designing authentic modeling tasks. In this study, we employed qualitative case study methods to investigate how elementary teachers designed and implemented authentic mathematical modeling tasks, with an explicit focus on how their tasks evidenced different dimensions of authenticity. We analyzed three cases of teams of elementary teachers as they developed modeling tasks connected to school and community contexts. The three cases were: 1) a student-driven modeling task related to paper and plastic waste in a school cafeteria, 2) a modeling task based on authentic situations at a community-run resource center, and 3) a modeling task focused on designing and monitoring a school community-building art project. Our cases illustrate that elementary teachers can successfully design and implement modeling activities that utilize different entry points and evidence multiple dimensions of authenticity. Furthermore, we found that the specific dimensions of authenticity may vary depending on the design supports and curriculum challenges within each context.