Through a qualitative multiple case study, the researcher’s goal in conducting this study was to investigate and understand the experiences of five upper elementary teachers in grades three through five who transitioned from traditional grading practices to standards-based grading (SBG) practices at one elementary school. Using Albert Bandura’s Social Cognitive Theory (SCT) as a framework, this study examined how the five teachers experienced the initial training and subsequent implementation in their transition from traditional grading practices to standards-based grading practices. The researcher also aimed to understand teacher self-efficacy toward the new grading practice based on the training received at the onset of the implementation. A recruitment survey was sent to 79 certified teachers at the study site, chosen based on its convenience and recent implementation of SBG, and yielded the minimum of five participants meeting the criteria to participate in the study. Two of the total five study participants were part of a pilot study conducted in the fall of 2019. The researcher conducted semi-structured face-to-face interviews using an interview protocol established in the pilot study. In order to identify underlying themes present in the five interviews, the researcher used a constant comparison method of analysis (Leech & Onwuegbuzie, 2007). Common themes present in the five case studies include grades as communication, frustration with SBG transition, support from colleagues as useful or not useful, and lack of preparation at the pre-service level. Findings from this study align with the current body of knowledge on the inequities present in the use of traditional grading, the lack of specific grading instruction in teacher preparation programs as well as continued support at the district or school level, and the positives of SBG moving teachers toward best practices. Findings from this study also support teachers’ self-efficacy being tied to the quality of training they receive when making a change in practice.