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Following Juvenile Life Without Parole (JLWOP) reform, courts must consider the “hallmark features of youth” in resentencing, yet how these concepts are interpreted remains unclear. Using courtroom observations and transcript analysis, this study examines how legal actors collectively define and apply developmental factors over time. Findings show that actors develop a shared framework that is strategically used by both sides and later adapted by judges, particularly on appeal, to align with higher court guidance. These results highlight the challenges of implementing reforms that require shifts in legal interpretation and the key role of appellate courts in shaping their application.