Educational leadership preparation is not an explicit priority in the scholastic formation of future Catholic priests in the Philippines. Consequently, there may be those assigned to lead in parochial mission schools early on in their ordained ministry but lack leadership training and experience. Thus, this study sought to answer the following research questions: What are the experiences of educational leadership successes and challenges of newly ordained Jesuit priests assigned as directors of Jesuit mission high schools in the Philippines? What are the perceptions of newly ordained Jesuit priests assigned as directors of Jesuit mission high schools in the Philippines on how their seminary formation contributed to their preparation as school leaders? This phenomenological research explored the experiences of seven first-time Jesuit school directors of mission high schools in the Southern Philippines and examined their perceptions about the leadership formation that they received as seminarians before being missioned to the ministry of leading high-needs schools in the peripheries of rural Philippines. Through a modified educational leadership preparation framework presented originally by Capper, Theoharis, and Sebastian (2006), I analyzed the qualitative data from the field and determined how the participants’ peculiar leadership experiences and keen assessment of their seminary formation can inform enhancements in the Jesuit leadership formation’s context-specific curriculum, andragogy, and holistic evaluation to prepare future Jesuit educational leaders’ critical consciousness and socially just leadership knowledge and skills. In line with this, I recommended the institutionalization of programmatic leadership training modules for Jesuits before they are missioned as first-time school directors.