For several decades, a shortage of school psychologists has been anticipated when the baby boom generation reached retirement age. Projections forecast that the worst of the shortage would take place in the latter half of the current decade. The present research investigated the experiences and perspectives of stakeholders in a mid-Atlantic state as they related to a possible school psychologist shortage. Ten individuals were interviewed with roles in public school districts, university training programs, and state-level organizations. Interviews revealed that, in the spring of 2017, there was no shortage in the classical sense of positions going unfilled. To date, the supply of new school psychologists has been sufficient to fill vacancies in the state. Many participants felt there was a shortage in the sense that they did not have enough school psychologists to meet school needs, however, and district directors sought the creation of additional positions. Interviewees reported that in recent years their psychologist-to-student ratios have increased, applications for open positions and internships have decreased, and student needs seem to be getting more complex. There were significant differences between the perspectives of trainers and non-trainers, with the latter advocating more strongly for changes at the university level. Comparisons between districts’ geographic setting (i.e., urban, suburban, or rural) revealed greater differences within geographic settings than between them. Instead, psychologist-to-student ratio was more influential on interviewee experiences. There were a limited number of proposals and implications for policy changes to counteract a shortage. In most cases, they would require a significant reconceptualization of school psychologist training or practices.