As we move towards the third decade of the 21st century, the development of emerging technologies continues to grow alongside innovative practices in digital media environments. This chapter presents a comparative case study of two teams (Team A and Team B) in a professional master's program during a 13-week, project-based course. Based on the role of documentation and the reflective practitioner, team blogs representing learner experiences of Agile practices were analyzed. This case study chapter focused on one blog post of a mid-term release retrospective. The results of this case study are framed around Derby and Larson's (2006) Agile retrospectives framework, including: set the stage, gather data, generating insights, deciding what to do, and closing the retrospective. The case study results suggest the need for public documentation of retrospectives and how this can be challenging with non-disclosure agreements. Also, the authors identify the importance of being a reflective practitioner. Future research on educational and professional practices needs to be explored.