In this article, we describe lessons learned from three separate literacy professional learning initiatives that took place in elementary schools in three different locations: high-poverty urban, medium-poverty rural, and low-poverty suburban. The professional learning initiatives were also diverse in scope: one was a three-year, school-wide partnership; one was a multiyear collaboration with two teachers; and one was intensive coaching of an individual teacher. Each initiative was (a) informed by previous research on literacy professional learning, (b) grounded in social constructivism, and (c) a design-based research study. Through collaborative analysis of data, we discovered shared barriers that impeded each of the initiatives from promoting substantial change. We suggest ways to improve literacy professional learning to better increase the odds of success and lasting change in literacy instruction.