In discussing education portals and the Web, Richard N. Katz & Associates (2002) state that the Web is the ultimate frontier. Katz observed that this frontier is inherently messy and in need of guidance, “if not law and order.” In this context, a portal is more than a gateway. It has the potential of functioning as a unifying principle around which educational institutions can leverage their resources, talents, and vision (Richard N. Katz & Associates, 2002). The Milwaukee Professional Support Portal (PSP) is a case study in how the development of an educational portal can serve as an agent for district-wide reform, while at the same time responding to specific needs for collaborative online venues, data warehousing, and personalized access to online information. This article examines the conditions that motivated the creation of the portal, traces how human dynamics contributed to the portal’s development, and follows the interaction between portal infrastructure and culture change. It concludes with a discussion of district adoption and scaling.