The work of teachers and students in secondary classrooms is infrequently connected to the United Nations’ Sustainable Development Goals (SDGs). In fact, the literature outlines a regular disconnect of learners’ experiences in the natural world from the lessons that they are taught. Public schools are not noted for producing connected learners who can generate the actions required to support heathy communities. This chapter describes the case of a partnership between Engineering students and teachers-in-training at one U.S. university. This collaboration sought to expand teachers’ training to devise authentic assessment tasks that situated discussion of the SDGs within an analysis of local sustainability. By perceiving design as an open process which democratically includes a range of stakeholder voices, trainee-teachers in this program considered alternative assessments that employed principles of design in their locality. This paper will offer insights from university instructors and students about the challenge of including participatory design practices within an established assessment protocol in teacher training. This case discussion will encourage university programs to consider collaborations in teacher training and to seek opportunities to design classroom assessments that connect students with challenges to be addressed in their localities.