Purpose: This study aimed to describe the subjective well-being of experienced special education teachers in one mid-Atlantic state in the United States. The significance of this study was amplified by the onset of COVID-19. These circumstances were reflected within the data and provide implications for school administrators. Methods: Qualitative data collection methods, including semi-structured interviews, focus groups, and audio journals, were used to generate data from twelve experienced special education teachers. Research Design: A transcendental phenomenological methodology, framed within Martin Seligman’s well-being theory, structured this study. Findings: The themes that arose from the data indicated that experienced special education teachers sourced positive emotions, engagement, relationships, meaning, and accomplishment from role-related experiences. However, barriers to these elements of well-being and negative emotions were also described. Some of this data aligned with previous literature and some data was shaped by the unique experiences of early pandemic virtual instruction. Conclusions: Culminating from the data are practical implications for K-12 school leaders to provide intentional support for the retention and well-being of special educators. Of these implications, acknowledging the hefty paperwork demands within the role, prioritizing teacher planning time, and expressing appreciation could benefit the well-being of those who teach within the special education community.