In the present study, the role of five categories of characteristics of a reciprocal peer coaching context was studied in relation to teacher learning. Both self-reports and student perceptions were used to measure teacher learning. Data were gathered on 28 secondary school teachers (14 coaching dyads). A mixed-method approach was adopted combining quantitative and qualitative data. To study the associations between five categories of characteristics of a peer coaching context (independent variable) and teacher learning (dependent variable), questionnaire results (quantitative data) and digital diaries (qualitative data) were examined. It was found that teachers learn when they are intrinsically motivated to take part in professional development programs; when they feel a certain pressure toward experimenting with new instructional methods; and when they are able to discuss their experiences within a safe, constructive, and trustworthy reciprocal peer coaching environment.