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This study aimed to conduct a historical review of the technology improvement project (TIP) at a local high school in Jamaica. More specifically, the project evaluated the TIP using Kotter’s 8-steps to organizational transformations. The review/evaluation is critical as the school moves to look at its strategic plan for the next 5 to 10 years as they emerge from the emergency they were thrust into with the pandemic. The research was conducted using the case study qualitative research methodology. The key research finding is that successful whole school change must include all stakeholders at the school including administrative staff and parents.