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This design case follows the instructional planning and decision making before and during a nine-week project-based unit co-taught by three of the authors at a not-for-profit charter high school in the American Southwest. The school serves students who have not been well served by traditional schooling. The teachers partner with industry professionals to create authentic learning projects. The project detailed in this design case aimed to have students design and test temporary shelters for people who were homeless, and later learn about semi-permanent shelters. Students consistently sought to design longer-term solutions to homelessness, rather than shorter-term solutions for individual homeless clients. An embedded researcher documented project implementation and design conversations—including formal planning prior to and emergent conversations during teaching. Analysis of these conversations reveals that many design decisions made prior to instruction were guided by learning objectives, constraints and opportunities, whereas those made during teaching practice were focused directly on supporting learning. Analysis also made clear that students played a role in steering the project to focus more on solutions to long-term homelessness; based on student interests, the final project included writing letters to government representatives about their ideas for solutions. The design case concludes with reflections by the teachers on the design decisions and attendant learning. This case helps to clarify how context and timing influenced design decisions and provides an exemplar of teacher-designed complex instruction, illustrating how learners might take part in reframing a problem about which they are learning.