We build on the approach of treating learning as a cross-setting phenomenon, exploring how the learning sciences might critically and expansively re-conceptualize resources for nondominant youths’ learning. First, we explore the range of ways the learning sciences has positioned settings theoretically and analytically, and some conceptual consequences of these choices. We then describe a cross-setting approach that de-centers schools as a primary analytical site for learning disciplinary content, and instead treats them as part of a larger ecology in youths’ lives. We share analyses of two episodes from one youth’s learning pathway to illustrate how a cross-setting analysis can expand a single-sited conceptualization of his resources for learning, in this case to include relational practices. This paper advances current scholarship on learning across settings by examining closely and empirically how cross-setting approaches might productively trouble and re-configure how we conceptualize nondominant youths’ lives in the learning sciences.