High teacher attrition rates are problematic for educational organizations. School districts need to exert greater effort to retain teachers due to the financial and student achievement costs associated with the constant churn. The purpose of this study was to investigate the perceptions of highly effective teachers regarding aspects of their working conditions that influence their willingness to remain in the profession. Additionally, the degree of influence that these factors contribute to teacher willingness to work at hard-to-staff schools was explored. Using a quantitative survey design methodology, 177 teachers in a large southwestern school district were invited to respond to an online survey. Respondents were asked to rate their level of satisfaction or agreement about perceptions of empowerment, facilities, resources, time, leadership, professional development, and mentoring at their present school sites. The study yielded a response rate of 20 teachers of the total highly effective teachers identified. Data analysis procedures included descriptive statistics. Comparisons were made between these highly effective teachers and larger samples of teachers who previously responded to a similar survey. Study findings indicated that this subset of teachers believed that teacher empowerment and facilities and resources are the most important factors in promoting student learning. However, the most influential factors that highly effective teachers maintained would lead to their willingness to remain in teaching were school leadership as well as school facilities and resources. Moreover, the teachers indicated that they were adequately prepared to work in hard-to-staff school. Any reservations they had about working in these contexts stemmed from a perceived lack of support from various constituent groups such as school leaders, parents, and the community.