Thesis advisor: C. Patrick Proctor / Schools, districts, and states are at a time of transition from the federal No Child Left Behind Act (NCLB) to The Every Student Succeeds Act (ESSA) and this change comes alongside evolving state policy landscapes. Since NCLB and the epoch of English-only education in Massachusetts, which ended after the passage of the Language Opportunity for Our Kids (LOOK) Act in 2017, have been shown to have a primarily negative impact on emergent bilingual students, a historically marginalized group of learners, there is a need for educators and researchers to understand how educators are comprehending and responding to policy changes. Yet processes of policy interpretation and implementation are often not straightforward and many factors from the location of an organization to an individual’s role, connections, and prior professional experiences (Burch & Spillane, 2005; Spillane, 1998) can impact policy understandings and implementation. The purpose of this qualitative dissertation was to understand how educational leaders interpreted and responded to ESSA and the LOOK Act in Massachusetts. Utilizing sensemaking theory as a theoretical framework (Spillane, Reiser, & Reimer, 2002), analysis of 17 participant interviews as well as state documents demonstrated that district, state, school, and organizational leaders were optimistic about the educational future of bilingual children in Massachusetts. They viewed the LOOK Act as offering needed flexibility for designing educational programs, as better aligning with participants’ beliefs about bilingualism and language learning, and as potentially facilitating the increased engagement of bilingual families as stakeholders with a voice. Educational leaders understood ESSA in relation to how they understood NCLB. They also viewed ESSA primarily as a compliance mandate. Participants responded to ESSA and LOOK by defending their intentional focus on the immediate: the policies, initiatives, and practices that aligned with their beliefs about what is best for bilingual students. These priorities included reconceptualizing programs of education for bilingual students and launching English Learner Parent Advisory Councils, both made possible by the LOOK Act, as well as hiring and retaining equity-minded district leaders, advocating at the state and district levels around funding structures, building teacher capacity to teach emergent bilingual students, developing multiple pathways for children, and shifting belief systems around bilingualism and bilingual children. Developing understandings of how educators interpret and respond to ESSA and LOOK can further inform educators’ crafting of policies and programs that can benefit bilingual children. / Thesis (PhD) — Boston College, 2019. / Submitted to: Boston College. Lynch School of Education. / Discipline: Teacher Education, Special Education, Curriculum and Instruction.