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This exploratory study addresses pervasive teacher shortages by examining the paraprofessional Grow Your Own (GYO) residency pathway at a Hispanic Serving Institution. Utilizing a mixed-methods design with surveys, interviews, and institutional data, the research investigates key design elements, student challenges, and outcomes. Findings reveal that while paraprofessionals demonstrate strong classroom performance due to their prior experience, they face significant systemic barriers. Key challenges include balancing dual roles, time constraints, and particularly, struggles with certification exams, leading to lower certification and employment rates. The study underscores the need for enhanced, personalized support, dedicated study time, and improved job placement after residency to fully leverage this vital pathway for diversifying the educator workforce and addressing high-need areas.