These three condensed design cases provide a glimpse of the decisions undertaken by novice designers in a graduate-level message design course. The course helps students examine the role of communication theory, cognitive psychology, cultural influence, and design skills within the context of instructional messages both in theory and through practical application. Practical application in the course includes smaller design projects to gain experience with best practices and recommendations, and the course culminates with a service learning project that pairs students with a community partner. The community partner provides basic specifications for a specific need, and the students then design artifacts to meet these requirements. The assignment is evaluated based of how well students followed client specifications, design considerations for each medium, content and grammar mechanics, copyright guidelines, and general design principles. However, the students also compete in the sense that the client selects which artifacts to implement from among those submitted. Embedded within each design case are instructor reflection comments that address particular or repetitive themes that emerged from each designer. Combined, these cases help identify course design weaknesses and bring clarity to concerns regarding how to help novice designers progress in competency.