This is an investigation of secondary mathematics teachers' understanding of performance-based tasks with respect to the contextual design of tasks that promote urban students' engagement and pursuit in learning mathematical concepts. We examined the alignment of teacher designed tasks with their personal definitions of tasks; then further analyzed the teacher designed tasks with respect to the literature on effective performance-based tasks and culturally relevant pedagogy. We found after a yearlong engagement in professional development teachers were able to analyze tasks for cognitive demand. However, the teachers were not as adept in creating culturally relevant tasks of high cognitive demand. (Contains 5 tables.)