Many scholars have written about the impact of the First Intifada (1987–1994) on Palestinian education in the Occupied Palestinian Territories (OPT). The era was marked by prolonged school closures, violence against children, and widespread protests across the OPT. Students, teachers, and families in the education sector of East Jerusalem, however, experienced the Intifada in distinctive ways compared to the rest of the OPT due to the city’s particular status as both occupied and annexed by Israel since 1967. To build on the existing literature on the First Intifada's impact on education in the West Bank, this paper explores how East Jerusalem's Palestinian community leaders, educators, and students shaped their own educational paths during the tumultuous era of the First Intifada. The paper draws on historic newspaper articles as well as oral history interviews conducted with Palestinians in East Jerusalem between 2021 and 2023. The oral history narrators included former students and teachers who had navigated the era from within East Jerusalem's fragmented school system, filled with Israeli-run public schools, UNRWA schools, Christian private schools, independent private schools, and private schools run by the Jerusalem Islamic Waqf. The expansive private school sector, created by Palestinians after the 1967 Israeli occupation as a way to escape the Israeli-controlled public education system, housed a majority of East Jerusalem’s Palestinian students. This paper argues that the private school system managed to partially spare some Palestinian students from the Intifada's education disruptions and allowed Palestinians in the city to retain some indigenous governance over their own education through the First Intifada era. However, the cumulative impact of school disruptions and Israel's intensification of the legal and physical separation between East Jerusalem and the West Bank during the First Intifada and subsequent Gulf War challenged East Jerusalemites' ability to maintain the parallel education system that they had fought so hard to create due to the financial strain it placed on the schools during an already difficult economic time. Meanwhile, as the Palestinian school system in East Jerusalem struggled, the teachers and students within it also walked a tightrope—each balancing their educational aspirations and careers with their desire to resist the Israeli occupation.