When it comes to implementing innovative classroom technology programs, urban school districts face significant challenges stemming from their big-city status. These range from large bureaucracies, to scalability, to how to meet the needs of a more diverse group of students. Because of their size, urban districts tend to have greater distance between the chief technology officer and those who actually use instructional technology, with separate reporting hierarchies often leading to "silos" and insufficient communication--a problem that can be exacerbated because employees' offices are geographically dispersed rather than centrally located. Despite these challenges, there are urban districts that have managed to implement bold technology initiatives. In looking at their stories, certain common themes--like buy-in, flexibility, professional development--emerge as essential elements to achieving success on the larger playing fields of big-city schools.