As much as it is eagerly anticipated, freshman year is often a time of confusion, disorientation, and even alienation for many students. One in four college freshmen will drop out before completing sophomore year. The reasons for this high level of withdrawal vary, but a report suggests that new students often feel overwhelmed and unprepared for the academic and social challenges of college life. Higher education institutions are constantly looking for new ways to help first-year students smooth the transition between high school and college. Many begin before the students even step foot on campus, investing in sophisticated web portals for prospective and admitted students that provide a gateway to relationship building with faculty, staff, and other incoming freshmen. Most colleges and universities also commit administrative resources to helping new students get acclimated to campus, creating departments with titles such as the Office of Retention and First-Year Programs. Yet not many universities devote the same level of IT resources to students once they arrive, as they do to encourage them to come. And few provide their first-year program administrators with technological tools that will help them proactively support students. At most, freshmen are directed into the same portal all students use, or have access to a static web page featuring a "frequently asked questions" list and links to the offices and groups a freshman might find useful. Higher education IT experts can point to a handful of universities, however, that have developed first-year student portals in an effort to reach out to this vulnerable population. The innovative administrators behind these programs have sought to move beyond passive websites to create personalized and event-driven pages with information pushed to students based upon their needs and interests. While most of these pioneers cannot pinpoint the actual impact of the portals on retention rates (because the programs are either too new or they are just one part of a broader first-year support effort), they believe the portals are forging deeper bonds with their first-year students by proactively targeting their social and academic needs. This article presents three case studies.