Background: Despite considerable investment in UK government initiatives (e.g., the Physical Education School Sport [PESS] plan) aimed at improving the delivery and quality of physical education (PE) in primary schools, many remaining problems have been highlighted (e.g., facilities; staff training). It is suggested that the head teacher (school principal) plays a fundamental role in the experience of PE delivery within their schools as well as the effective implementation of government initiatives (e.g., PESS) that aim to enhance the quality of PE within primary schools. However, this role has been previously overlooked in the literature. Purpose: This study offers an in-depth examination of the challenges faced by primary school head teachers in effectively creating and managing an environment that supports high quality PE and school sport. The study also explores the head teachers' perceptions of the challenges caused by the implementation of the PESS plan within their school. Participants: 14 head teachers of primary schools located in the same local authority agreed to participate in the study through the provision of informed consent. The participants ranged in age from 45 to 61 years, had held their position between 6 and 10 years, and included 5 males and 9 females. Research design: A qualitative approach using a semi-structured interview design was employed. Data collection: Participants were sent an interview preparation booklet one week prior to their individual interview date in an attempt to aid memory recall and improve the flow of the interview. During the interview itself, participants were guided through a semi-structured interview process that consisted of six sections but remained flexible in attempts to enhance the depth and quality of data collection. Data analysis: A combination of both inductive and deductive content analysis procedures were applied to each interview transcript with trustworthiness characteristics being considered throughout the analysis procedures via thick description, the recording and transcribing of all interviews, triangulation, peer debriefing, and member checking. Findings: The participants reported a number of issues relating to the provision of high quality PE including: (a) school policies; (b) the curriculum; (c) extra-curriculum provision; and (d) resources and finance. Participants also acknowledged the challenge of implementing and managing the PESS plan and outlined some initial problems with the initiative. Benefits of the PESS initiative in raising the standards of PE delivery were also reported. Conclusions: The head teacher faces many challenges when it comes to creating and managing an environment that supports high quality PE provision. Although some aspects of these challenges are out of the control of the head teacher (e.g., government targets; access to facilities), it would appear clear that a commitment to PE provision by head teachers would result in greater strategic planning and use of resources to support their staff in implementing PE policy. Consequently, the role of the head teacher in ensuring a specific policy is developed for PE that considers the wider targets of government PE initiatives and that encourages the development of effective, high quality PE cannot be underestimated.