Massachusetts has received $2.9 billion in Elementary and Secondary School Emergency Relief (ESSER) funding, with the vast majority going to districts. Across the state, almost all of the first round of funding (ESSER I) and the majority of the second round (ESSER II) has been spent. Districts now have until September 2024 to spend the remainder of the third round of funding (ESSER III). How is this money being used? And what challenges do districts face in spending such a large amount of money effectively? To find out, our EdImpact Research Consortium created a Data Dashboard to track and analyze spending in 24 key districts. But the numbers alone don't tell the whole story. To dig deeper into the successes and challenges districts have faced in allocating ESSER funding, we also produced this case study that takes a closer look at what this process looks like for Holyoke Public Schools, New Bedford Public Schools, Revere Public Schools, and Worcester Public Schools. Through data analysis and interviews with district staff, this case study explores these districts' journeys to address students' lost learning time, the ways they have chosen to use funds, and some of the most expensive items in their ESSER plans. [This report was prepared with EdImpact Research Consortium, a collaboration between the Rennie Center for Education Research & Policy, the CERES Institute for Children & Youth at Boston University Wheelock College, Education Resource Strategies (ERS), and the Massachusetts Business Alliance for Education (MBAE).]