Student affairs practitioners begin their professional experience through graduate assistantships, which, in conjunction with their classroom learning, prepare them to meet many entry-level competencies needed to succeed in student affairs. There is a tremendous amount of learning derived from graduate assistantships, and it may be beneficial for graduate student affairs professionals to become aware of the moments when they are learning. Doing so may help them understand how they learn and how they make connections between their academic and on-the-job learning for their future practice. Research around the utilization of metacognitive strategies such as reflection and emotional regulation in professional practice has found that participants foster a deeper understanding of their experiences and are able to recognize their learning more readily. In order to understand how to cultivate metacognition into professional practice, a deeper understanding of the environments and contexts of graduate student learning in professional practice is needed. This study explored awareness of learning among student affairs professionals in graduate assistantships, examining the interactions and environments that facilitated awareness of learning, how participants described their learning, how they became aware of their learning, and the emotions they associated with their learning. A case study approach explored the experiences of nine participants who were enrolled in their first year of a graduate program in higher education and student affairs. Qualitative data was collected through a focus group, reflective journaling practice, researcher observations, and a document analysis. Findings from this research demonstrate connections between learning moments and the emotions experienced by graduate student affairs professionals during those moments, as well as the role that reflective practice had in regulating emotions. Data also emphasized the role that the supervisor-supervisee relationship plays in learning consciousness and emotional regulation, and how motivation and resilience influence emotional regulation, learning connections, and self-authorship within the profession of student affairs. The findings of this study provide several implications for practice such as integrating emotional regulation and reflective practices into professional development, intentionally creating strong supervisorv supervisee relationships, and establishing graduate assistantship seminar courses in graduate preparatory programs in the field of student affairs.