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Education for working learners takes many forms – degree seeking, online self-access modules, and on-the-job training. Employers have publicly encouraged working learners’ participation in educational programming, yet fail to support or recognize workers’ efforts. Drawing from Critical Race Theory (CRT) and Cultural Historical Activity Theory (CHAT), this study examines perspectives about employer-supported education. Findings indicate that open opportunities for skills development supports success on the job and may also impact workers’ daily life. Working learners need to be understood as a key component of the learning ecosystem rather than passive recipients, and programming needs to be aligned with working learners' motivations and goals. Issues such as race, language, and socioeconomics play an important role in the health of learning ecosystems.