The transition to a new architecture and design for an academic library Web site does not always proceed smoothly. In this case study, a library at a large research university hired an outside Web development contractor to create a new architecture and design for the university's Web site using dotCMS, an open-source content management system. The library participated in the design and development process along with other campus units. Because the university-wide process focused on marketing the university to prospective students, parents, and donors, the contractor's fact-finding process focused on how the library's site design could incorporate Web 2.0 technologies. The resulting library Web site showcased Web 2.0 technology more than it provided users with access to library resources. The library's users quickly communicated their dissatisfaction and confusion, which led to some immediate changes and a commitment to redesign the site based on expressed and demonstrated user needs. The library then hired another contractor to conduct iterative usability testing on both the new site and prototypes for a redesigned version. The testing showed that Web 2.0 technology that does not meet existing user needs creates obstacles for both novice and experienced users. In collaboration with the university's information technology unit, the library developed and launched a revised Web site, which helped users connect to the resources they needed. In the upgrade, Google Search Appliance replaced the native dotCMS search functionality. The authors of this case study demonstrate that libraries may need to advocate for different Web design priorities than those used at the university-wide level and that working with outside contractors presents different challenges and opportunities depending on the contractor's hiring unit. These experiences also demonstrate that libraries can do a better job learning about their users when they lead the fact-finding process. Following these experiences, the library committed to conducting iterative usability testing on a regular basis.