Small City School Districts across New York State are becoming increasingly fearful of losing newly hired, highly talented teachers. In the United States, 8% of teachers leave the profession annually and greater than 50% quit teaching before reaching retirement age (Sutcher, 2016). A study done on teacher retention decisions in New York City revealed lack of administrative support as one of the top five reasons for teacher attrition (Boyd, Grossman, Ing, Lankford, Loeb & Wyckoff, 2011). The importance of a teacher's effect on student achievement cannot be overstated. Teachers have more influence on student achievement than any other factor (Carver-Thomas & Darling-Hammond, 2017). The purpose of this quantitative study was to investigate the effect that high school principals have on the retention of high school teachers in Small City School Districts in New York State. This research examined the responsibilities of high school principals who are important to teachers' decision to remain in their current role; determine which responsibilities exist in their schools; and analyze the correlation between the two. The leadership practices and principles that are defined in The 21 Responsibilities of the School Leader, as outlined by Marzano, Waters and McNulty's book (Marzano, McNulty, & Waters, 2005) School Leadership that Works, are the conceptual frame for this study. This study utilized anonymous survey results from 295 respondents currently employed in 13 Small City School Districts located within the Northeastern Regional Information Center of New York State. The findings from the research indicate that while all of the 21 Responsibilities used in this research are existent, respondents were neutral in their perception of whether any of them were important to supporting teacher retention. However, when separating the results by demographics, there were significant differences by gender and years of teaching experience. Responses by females and teachers with less than 10 years' experience demonstrated statistically significant differences, whereas they perceive a vast majority of the 21 Responsibilities used in this study to be more important than their male and veteran teacher counterparts. Also, the Responsibility of Involvement with Curriculum, Instruction, and Assessment ranked last amongst survey results as important to supporting teacher retention and perceived existence by the building principal. Finally, all leadership behaviors used in this study demonstrated a moderately positive correlation between what was perceived as important to supporting teacher retention and perceived existence of the behavior by the principal. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]