Introduction: The school-to-work transition (SWT) is complex for young people. The postpandemic era, characterized by rapidly evolving economies and technologies, has augmented the complexity of negotiating such pathways. Despite this, young people--understood here through the lens of emergent adulthood--are often positioned as wholly responsible for navigating their own pathways beyond school. Methods: A pragmatic case study approach was used to analyze qualitative data collected from three SWT partnership programs (UniHub, Australian School-based Apprenticeships [ASbAs], and Regional Learning Pathways [RLPs]) aimed at young people (2018-2023) in regional areas of Tasmania, Australia. For each program, participants were interviewed (N = 6 [UniHub]; N = 23 [ASbAs]; N = 44 [RLPs]) and surveyed (N = 350 [UniHub]; N = 21 [ASbAs]), and data were thematically analyzed to identify the role of boundary-crossers in SWT partnerships. Results: Boundary-crosser work emerged as a key component of the sampled SWT partnerships. Enabling features of boundary-crossing work in partnerships include accessibility, support contextualized to the region and individual--like reducing barriers to equity--and using clear communication approaches. This role redistributed responsibility in the SWT to a partnership between schools, pathways, and young people. Conclusions: Whereas literature and policy underscore the economic and developmental importance of SWT, the contribution of this article is research and data that nuance understanding of how SWT partnerships can share the responsibility of the SWT by designing in the program a boundary-crosser role. The concept of boundary-crosser work in SWT partnerships offers a novel approach for policymakers in policy and practice to rethink how the SWT is supported.