BACKGROUND: School closures and service disruptions related to the COVID-19 pandemic significantly impacted students’ postschool transitions. Students with disabilities who were also members of historically marginalized groups including immigrant students, multilingual students, students of color, and those experiencing poverty, were disproportionately negatively impacted by pandemic-limited services. OBJECTIVE: This paper examined the impact of the pandemic on the transition experiences of secondary students receiving both special education and English learner services. METHOD: We collected and analyzed data from ethnographic interviews with 26 students, their parents, and teachers. A close analysis of a representative case illustrates how transition education and planning were affected by challenges introduced by the COVID-19 pandemic for some of the nation’s most vulnerable students. RESULTS: Despite postsecondary education goals and high parent expectations, evidence of minimal information sharing between school and family, specific plans for goal actualization, and interruptions to service delivery negatively impacted goal attainment, tipping precariously positioned transition plans toward missed opportunities. CONCLUSION: The pandemic accentuated pre-existing inequities in transition and vocational rehabilitation (VR) services. Implications for practice and research are discussed, including the importance of supported family engagement, enhanced self-determination skills, and integrated VR services into high school special education programming.