This qualitative study chronicles the narratives of three mothers whose children transitioned from elementary to middle school. Each participant was interviewed on three occasions to capture their lived experiences in what often has been considered a tumultuous time for families. The interviews focused on the participants' experiences before, during, and after their child transitioned to middle school, created portraits of what participants felt their roles were in elementary and middle school, and identified resources the participants had available to them during the transition. Through qualitative data analysis techniques applied to the participants’ narratives, it was evident that the participants felt a lack of communication at the middle school level, experienced a sense of uncertainty regarding parental expectations in the middle school transition, and were unaware of how the middle school transition would drive their family’s daily routine. Additionally, the participants offered advice to future middle school parents and to schools to potentially improve the parental transition to middle school. The conceptual frameworks for this study were stage-environment fit theory, role exit theory, and role construction. Practical implications from this study include, but are not limited to, classroom teachers, schools, and school districts identifying the needs of their incoming middle school parents to best outfit them with the skillset needed to successfully navigate being a middle school parent.