The United States, along with the rest of the developed world, is experiencing a shortage of cybersecurity talent in the workforce ((ISC)[superscript 2], 2019). Among the strategies being encouraged and used to close this workforce gap are work-based learning programs like cybersecurity apprenticeships. Well-designed apprenticeships can provide a win-win-win situation for employers, students, and schools. This article describes our experiences to date working to establish a meaningful cybersecurity apprenticeship program. We share the early success we have found as well as some lessons learned.