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We conducted an exploratory case study design, using Cognitive Career Theory (SCCT) as our theoretical framework, to investigate how high school students’ career aspirations to pursue teaching can be influenced by the interactions of their self-efficacy beliefs, outcome expectations, personal goals, and other environmental and contextual factors. Our findings, while illustrative of great variability amongst our individual participants, were demonstrative of how positive teacher relationships and mentoring activities fostered an active interest in our high school students’ aspirations to teach. These results are illustrative of how high school students’ affective experiences and dispositions towards teaching can be influenced by environmental and contextual factors, and can inform the design of high school teaching pathway programs and recruitment efforts.