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Academic librarians voluntarily leave their positions for a variety of reasons, including factors related to work environment, compensation and benefits, and job duties. Results of a study we published titled “Contributory Factors to Academic Librarian Turnover: A Mixed-Methods Study” found that dissatisfaction with library leadership and direct supervisors, as well as low morale, are top factors leading academic librarians to resign. In our survey, several open-ended responses describe instances of bullying, neglect, favoritism, and unfair treatment by direct supervisors and library administration. These experiences suggest a larger trend of toxic library leadership within the academic library profession. The study concludes that dissatisfaction with library work culture and experiences with poor library leadership are precursors to low morale, and a connection exists between low morale and burnout, both of which are exacerbated by task overload, role ambiguity, budgetary pressures, and work-life balance. Finally, our study reveals several areas of job dissatisfaction related to inequitable access to the rights and privileges of faculty status and tenure where tensions exist among library workers classified as faculty or librarians versus those classified as paraprofessionals or staff. This chapter qualitatively explores the most salient factors contributing to individuals’ decisions to leave their jobs, discusses how these factors are symptoms of larger, systemic dysfunction at the organizational level within academic libraries, and proposes several ideas for library administrators to consider.