The concept of pavement management has been around since the late 1970’s. While the pavement management concepts remain the same, advancements in technology have been made in area of commercially-available pavement management software, including sophisticated user interfaces, linking with the latest GIS software, and webenabled products. Since 1987, the City of Calgary (City) has been using pavement management products to effectively manage their paved road network. As computer technology evolved and the pavement management need of the City changed, the migration from the Municipal Pavement Management Application (MPMA) to state-of-the-art client/server and web (browser-based) Highway Pavement Management Application (HPMA) seemed like a natural transition. HPMA is implemented and used by the Provinces of British Columbia, Alberta, Ontario, and Nova Scotia. Nevertheless, Calgary would be the first municipality in North America to implement HPMA. One of the key reasons motivating the City to move from MPMA to HPMA was the software’s capability to handle dynamic segmentation. Migrating the City’s data from a static block-to-block segmentation database to a dynamic segmentation database tied to the City’s GIS network presented some challenges. This paper presents the challenges encountered during the migration process and how the project team worked together to overcome these challenges. The paper also presents a comparison of results between the MPMA and HPMA databases, including the updated decision trees, the effect of the trees on the pavement network performance, and how the number of pavement sections changed due to dynamic segmentation. The paper also presents the GIS capabilities of displaying the condition of the pavement network.