This study documents opportunities for diverse adolescent English learners to deeply engage with content and language in flipped learning environments. Through a linked description of teaching practices and student learning experiences in an urban New England high school, the study attempts to understand the potential of flipped instruction in preparing a traditionally underserved population for post-secondary education. Our research partner Patriot High School (PHS) is one of the New England schools implementing flipped learning. PHS represents a typical secondary school context for adolescent English learners: More than half of students speak a language other than English at home and the majority of students are from minority and low-income homes (Massachusetts Department of Elementary and Secondary Education, 2014). PHS is also an urban school committed to implementing student-centered learning strategies to meet the needs of its diverse students.