Albeit deemed as the safest means of transportation by the National Highway Transportation Safety Board, pupil transportation services do encounter issues of negligence that expose school districts to litigation. This study examines the historical development of case law pertaining to mass pupil transportation systems, specifically bus driver actions from a legal perspective. This dissertation focuses on ways to assess the effectiveness of current preventative measures to preventing the act(s) that might be negligent or preventing a negligent action against a school district or its employee(s). This dissertation met these goals by examining current literature associated with pupil transportation as well as 105 court cases involving litigation from a variety of states and court jurisdictions. The cases briefed in this study are arranged by subtopic and peruse federal and state law accordingly. This research study produced a number of key findings relevant to pupil transportation employees and tort liability issues. First and foremost, the study provides an anlysis of cases pertaining to criminal background checks, medical conditions, and drug testing as a means of prohibiting individuals with problematic issues from attaining employment as a bus driver. Secondly, exposure to litigation through negligent acts of bus drivers and other affiliated transportation employees were addressed by examining negligence associated with arriving at/ waiting at the bus stop, while driving resulting in student injury, driver issues, driving a bus resulting in injury to property or others, alighting from a bus resulting in student injury, independent contractors, liability insurance, cell phones, and seat belts. The main conclusions drawn from this research were that current approaches to addressing negligence associated with pupil transportation were deficient because they failed to embrace the need for indepth training for bus drivers, teachers, building level administrators, as well as district level administrators. This research argues for thorough training conducted by a legal expert on an annual basis for all individuals affiliated with district pupil transportation services in an attempt to reduce the number of student injuries and/or fatalities associated with such services. Futhermore, this research agrues for the protection of school district finances through adequate training in an attempt to reduce litigation associated with pupil transportation and tort liability by foestering extensive communication networks to address problematic areas.