A range of efforts are underway to improve the effectiveness and efficiency of advising and student supports. Among these is the Integrated Planning and Advising for Student Success (iPASS) initiative. Launched in 2015, the initiative provided three years of financial, technical, and change management support to 26 two- and four-year institutions as they redesigned their advising processes and adopted and implemented new technologies. Over the three years of the grant, Achieving the Dream and EDUCAUSE provided strategic assistance to help institutions leverage both technology and human relationships to undertake a fully scaled redesign of their advising and other student support services. Concurrently, CCRC conducted a series of qualitative and quantitative research studies to understand how institutions approached their redesign and how this work affected students. This report shares the stories of the four community colleges that participated in the iPASS initiative. Each offers a unique example of how a community college chose to implement the iPASS approach, along with a discussion of the main elements of its advising redesign and its experiences with technology integration. After presenting individual case studies of the four colleges, the authors highlight cross-case lessons, which may be useful to college administrators, student services leaders, and advisors who are planning or implementing an advising redesign. As these stories illustrate, the advising redesign process is iterative, collaborative, and challenging, calling for multiple stakeholder groups across an institution to break down silos and work together to improve student outcomes.