School engagement is a multidimensional construct that includes behavioral and emotional dimensions that affect a student’s interaction with his/her school environment (Appleton et al., 2006). School engagement has been positively correlated with academic achievement, however there is a growing body of literature that has found the opposite is true with Black/African American students (e.g., Johnson et al., 2001) who have higher levels of school engagement yet lower levels of academic achievement than their White peers (Shernoff & Schmidt, 2008). Chapter One was a systematic literature review that identified study qualities, the role of culture, and hypothesized reasons for the existence of this engagement-achievement paradox. Results suggested there is a need to consider culture and teacher-student relationships when examining the relationship between school engagement and academic achievement. Chapter Two examined the relationships between cultural humility and emotional school engagement variables, the predictive value of teacher cultural humility on school engagement and academic achievement, and further explored the engagement-achievement paradox among diverse early adolescents. Data were gathered among 1,504 middle school students in a high-need, low-income school district in the Southeastern United States during 2018-2019. Students completed the Strengths and Difficulties Questionnaire (SDQ; Goodman, 1997), the Inventory of Teacher Student Relationships (IT-SR; Murray & Zvoch, 2011) and the Cultural Humility Scale for Students (CHS-S; Srisarajivakul et al., 2021). Results indicated that cultural humility correlated highly with other measures of emotional school engagement. When considering cultural humility, there was an engagement-achievement paradox among Black/African American students, highlighting the importance of culturally humble practices in teaching. Findings from this study have the potential to expand the school engagement literature base to include cultural humility and inform culturally-responsive teaching practices.