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In this study, we investigate how teacher retention rates differ by certification pathway and how individual characteristics and working conditions contribute to teacher retention. We specifically focus on how teacher retention pathways differ five years following certification, how these retention patterns hold across a decade, and what these patterns mean for historically excluded groups. Our results indicate that: a) traditionally certified teachers have higher retention rates than alternatively certified teachers, b) teachers of color were less likely to leave the field, and c) alternatively, certified teachers who share the same race as their principals were less likely to leave teaching. Our findings provide insights into how teacher certification pathways and teacher retention rates impact marginalized communities.