The shortage of teachers in regional and remote schools remains a pressing problem and has been exacerbated by the current national teacher shortage. The preparedness and willingness of graduate teachers to work in regional and remote areas are central to this problem. Partnerships between professional experience sites, providers of initial teacher education, and education systems are considered key to a successful professional experience placement, combined they can prepare pre-service teachers for future graduate employment. This qualitative study provides insight into the perspectives of professional experience site leaders to understand the benefits and challenges of professional experience and graduate employment in regional and remote schools and how to address these issues. The findings suggest that the benefits and challenges of professional experience and graduate employment in regional and remote schools are complex and shaped by various factors. Mentor teacher availability, limited uptake of placements by pre-service teachers, a limited understanding of regional and remote contexts, specific preparation, and general early-career teacher retention all contribute to the multi-pronged complexity inhibiting regional and remote employment. Benefits such as offering an alternative to a city-centric lifestyle, fast-tracked permanency, and financial incentives have shaped policy with limited success in addressing the teacher workforce crisis. Our findings suggest an alternative approach may benefit the issue of teacher shortage in regional and remote schools. We propose the widespread implementation of successful context-specific instruction as pre-service teachers prepare for professional experience in regional and remote schools as a possible means to address the long-standing regional and remote teacher shortage.