This paper examines technology-mediated advising reform in order to contribute to the understanding of how colleges engage in transformative change to improve student outcomes. Conceptualizing such change as occurring along three interrelated dimensions of organizational functioning (structural, process, and attitudinal), we seek to understand the contexts that encourage or discourage transformation of advising and student support. We use in-depth pre/post data from six colleges deploying integrated planning and advising for student success (iPASS) to investigate the reform process. Three of the six colleges made steps toward transforming their student support delivery, shifting along all three dimensions. We identify four contextual features that appear to underpin colleges' likelihood of transformative reform. Technology and vendor relationships form an important foundation. Reform vision and rationale, leadership, and the college's orientation toward student success are important institutional influences. Our findings support the hypothesis put forth by Karp and Fletcher (2014) in their Readiness for Technology Adoption framework that technology is necessary but not sufficient for transformation, and that project-level and organizational factors are perhaps more important. Moreover, the findings demonstrate that technology can spur substantial institutional change, but only under certain circumstances.