This quantitative study investigates the issue of teacher shortages, operationalized through emergency permit rates, within the broader context and specifically during the COVID-19 pandemic, while assessing the influence of leadership characteristics. Utilizing a decade of publicly available secondary data (2012-2022), the research sourced information from the U.S. Department of Education, Pennsylvania Department of Community & Economic Development, Pennsylvania Uniform Crime Reporting System, and Johns Hopkins University. The analysis was bifurcated into two distinct periods: a general overview from 2012-2022 and a targeted examination of the COVID-19 era from 2019-2022. A key challenge addressed was the multicollinearity observed among various variables, including Total Enrollment and Total Instructors (0.994), Total Enrollment and Instructor Spending (0.859), and several others. The study employed an iterative modeling approach to avoid this issue, strategically excluding one collinear variable in each iteration while maintaining all others. This technique aimed to reduce multicollinearity, thereby yielding more robust and distinct variable models. This quantitative study aimed to address several research questions. Firstly, it sought to determine if there was a statistically significant difference in teacher shortages, specifically attrition, both overall and during the COVID-19 pandemic. Secondly, it investigated the impact of leadership characteristics, including the Superintendent's years of experience, salary scale, education level, and tenure in the district, on emergency permit issuance among teachers in Pennsylvania, both overall and during COVID-19. Thirdly, the study examined the relationship between environmental factors such as total enrollment, number of instructors, violent crimes, all crimes, COVID-19 cases, and COVID-19 deaths, and teacher shortages associated with increased emergency permits, again both overall and during the COVID-19 pandemic. Lastly, it analyzed the relationship between economic factors including education spending, instructor spending, property tax, low-income enrollment, spending per student, and teacher shortages associated with increased emergency permits, both overall and during COVID-19. Based on the analysis of data spanning both overall and COVID-19 periods, this study proposes insights into the complex dynamics influencing teacher shortages and emergency permit issuance in Pennsylvania, offering implications for educational policy and practice. Rooted in social systems theory by Parsons (1937), school climate theory by Cowen (1960), and educational leadership and management theory by Leithwood et al. (1999) the study explored the interconnectedness of socioeconomic factors, school environments, and leadership characteristics with teacher shortages. Employing advanced statistical methods including Multiple Regression and correlation analysis, the research identified significant positive associations between emergency certifications and the COVID-19 pandemic (p < 0.005). Additionally, it revealed a positive correlation between the superintendent's annual salary and emergency certifications across both periods, suggesting that higher salaries were associated with increased emergency certification rates. Conversely, during the COVID-19 years from 2019 to 2022, there was a notable shift in the significance of superintendent experience, with more experienced superintendents linked to a reduced incidence of emergency certifications during this period. The study also found consistent positive correlations between crime rates and total enrollment with emergency certifications for the period 2012-2022, indicating that increases in these factors were associated with rising emergency certification rates. Furthermore, it observed a significant negative correlation between total instructor numbers and emergency certification, suggesting that an increase in instructors led to a decrease in the issuance of emergency certification. These findings underscore the complex interplay between environmental, economic, and leadership variables in shaping emergency certification trends, providing valuable insights for educational stakeholders and policymakers grappling with teacher retention challenges, particularly in times of crisis in Pennsylvania, especially under the strains of the COVID-19 pandemic. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]