We seek to guide design, development, and adoption of Renewable Assignments by testing ways learners can contribute to Open Educational Resources (OER). We design, test, and iterate four assignment structures to this end. Testing was completed in an upper-division undergraduate endocrinology course, taught emergency remote due to COVID-19. Using mixed methods: surveys, focus groups, and iterations, we assessed assignment structures and created design guidance for renewable assignments and open pedagogy. We find that in a remote course, these assignments were effective in advancing learning goals. Both students and teachers favored their inclusion in the course. Analysis revealed six design principles to maximize effectiveness of renewable assignments and courses, and empowering teachers and learners to contribute to open knowledge. These principles also provide insight to praxis related to theories of open pedagogy, scaffolding, peer interaction, and active learning.