Many youth worker professional development (PD) efforts tend to focus on individualized skill development, rather than learning as a contextualized phenomenon that impacts youth workers’ everyday experiences in the field. Youth worker learning is fundamentally embedded in a broader ecosystem of programs, institutions, and systems that influence how they make sense of and implement their learnings. Examining institutionalized experiences and how they shape youth workers’ response to PD requires attention to the larger ecology of the contexts in which they work. In this paper, I analyze a PD initiative facilitated by a school district in the Rocky Mountain West. Data collected during the PD show that participating youth workers made changes to their program systems. At the same time, participants reported a range of institutional constraints that did not cohere with the PD. I bridge sensemaking theory to research on youth worker self-efficacy to unpack youth workers’ reaction to and implementation of the PD, and I discuss implications for youth worker PD. I propose that PD efforts could more closely attend to youth workers’ institutional contexts.