As learning societies necessitate continuous education, a growing number of part-time programs are being offered. A key challenge for part-time programs is adequately supporting students in connecting their learning within the program to their work life, which in contrast to dual education is not part of the program. To better understand such boundary-crossing support in part-time higher professional education, this explanatory sequential mixed-methods study was conducted. A large-scale study, consisting of quantitative data analysis of the Dutch National Student Survey, confirmed that part-time programs (n = 600) differ in perceived boundary crossing, with a medium effect size of [eta]2 = 0.13, and that factors postulated in the literature are related. An in-depth cross-case analysis of the boundary-crossing support provided in four purposefully selected part-time higher education programs (with high and low perceived support) indicated that brokers, boundary objects, hybrid practices, boundary interactions, degrees of freedom, degrees of clarity, and supervision are ways to support boundary crossing. These findings provide actionable strategies by which part-time higher professional education programs can support student learning across contexts.