An XSEDE strategic goal is to extend use of high-end digital services to new communities by preparing the current and next generation of scholars, researchers, and engineers in the use of advanced digital technologies via training, education, and outreach. The mission of XSEDE's Under-Represented Community Engagement (URCE) program is to raise awareness of the value of advanced digital research services and recruit users from new communities. In collaboration with XSEDE training and education programs, the URCE program works with faculty and students that are non-traditional users of XSEDE resources and helps them utilize XSEDE's advanced digital research services and ecosystem. Over the past five years, the URCE program organized and facilitated training across the country at a variety of institutions ranging from small private Historically Black Colleges and Universities (HBCUs) such as Philander Smith to the University of Texas at El Paso, a large public Hispanic Serving Institution. Every URCE-led training workshop included extensive formative and summative evaluation, including longitudinal tracking of participant progress in engaging with XSEDE services in order to identify growth and persistence as well as barriers and opportunities. 85% (209/245) of URCE-led training event participants were first time XSEDE training registrants. After attending, 14% of attendees obtained access to XSEDE resources and more than 18% registered for additional training activities. This paper presents the strategies used to achieve these results.