Reflective depth provides insight into educators’ reflective thinking skills, which should progress from surface-level to deeper reflection with structured support over the course of a teaching career. This qualitative case study examined reflective practices among agricultural educators from student teaching through late career. Our guiding research question was, “What are agriculture teachers’ experiences with reflective practice?” Using case study methods, we explored reflective practice as an educational process. Twenty-four secondary agriculture teachers were purposefully selected through convenience and snowball sampling. Data were gathered through semi-structured interviews and triangulated using member-checking, memos, field notes, and reflexive journals. A narrative thematic analysis was conducted. Three coding cycles were applied to 161 reflection prompts, producing 26 categories, 7 subthemes, and 3 overarching themes. The three themes were observational reflection, pedagogical reflection, and social-emotional reflection. Observational reflection included two subthemes— “What went well? What didn’t?” and “What could be improved?”— and appeared most frequently among student teachers, declining among late-career teachers. Pedagogical reflection consisted of teaching methods, instructional planning, and classroom management. Earlier career teachers focused heavily on classroom management, while middle-career teachers emphasized teaching methods. Instructional planning progressed developmentally: student teachers reflected on day-to-day lessons, early-career teachers considered future reuse, middle-career teachers shifted toward curriculum-level planning, and late-career teachers questioned curriculum relevance and practical value. Social-emotional reflection included collaboration and self-awareness. Middle- and late-career teachers more frequently reflected collaboratively and demonstrated deeper self-awareness, progressing from reflections on teaching behaviors to reflections on personal values and beliefs. Social-emotional depth increased consistently with experience. Findings suggest that agriculture teachers tend to develop greater self-awareness and more critical reflective capacity as their careers advance. Future research should confirm these developmental patterns and identify strategies to support deeper reflection across all career stages.