In 2015, 26 broad-access two- and four-year colleges from various regions across the nation began steps to adopt or enhance technology-mediated advising practices in an effort to improve the way they support students. These institutions were part of the Bill & Melinda Gates Foundation's Integrated Planning and Advising for Student Success (iPASS) initiative, aimed at promoting technology-supported advising redesign with implementation guidance from Achieving the Dream and EDUCAUSE. Understanding the iPASS colleges' long engagement in advising reform provides insights about sustainable and scalable redesign strategies that may work well at other institutions. Based on interviews with college personnel, this brief discusses the iPASS colleges' experiences, achievements, and challenges. The authors' findings align with and build on CCRC's previous iPASS and advising redesign research, which recognizes several elements connected with successful redesign efforts: the importance of strong support from senior leadership; a focus beyond technology adoption that considers structural changes at the college that are central to the student experience and advising practice; and a clear shift in outreach and communication with students--both in-person and electronically--that is more targeted and personalized. This brief also discusses how the early adopter colleges have worked with technology vendors, the ways in which they have leveraged internal resources to move the redesign work forward, and how they have maintained momentum in reform over a substantial period of time. [The report is funded by the Advising Success Network. An additional partner of the network is NACADA: The Global Community for Academic Advising.]