In recent years, the widespread availability of networks and the flexibility of Web browsers have shifted the industry from a client-server model to a Web-based one. In the client-server model of computing, clients run applications locally, with the servers managing storage, printing functions, and network traffic. Because every client is independent, each must have all relevant applications installed, patched, and updated, and developers must create applications for the range of computing devices and platforms in use. Web-based applications utilize Web browsers as a common interface to access servers where applications are hosted and processed. Users only need a computing device with a browser application and a network connection to use a range of tools. This article offers several questions that will guide a district's decision to transition from client-server model to a Web-based one.