This qualitative case study responds to calls for research on the ways critical reflection develops in preservice and novice teachers. While evaluating capacity to reflect is a dominant practice in teacher education, few studies explore empirically how different factors impact teachers' reflection. Building from earlier research that conceptualized a typology that included four levels of reflective thinking, this study explores how different factors spur the highest form of reflection identified by the literature, critical reflection, through a multi-method approach involving several sets of data across nine cases of learning to teach. Findings from within-case analyses suggest some habits of critical reflection transfer across contexts, while others appear to be contextually dependent. Shifts in teaching contexts and elicitation practices appear to drive the quality and quantity of critical reflection suggesting that some habits of reflection can be elicited and reinforced by teacher educators regardless of context.