Local newspapers have become fixtures in communities as archivists, watchdogs over people with power, and as trusted sources for information and analysis. This thesis examines the challenges newspapers face as they reinvent themselves as digital media companies. When a legacy company attempts to innovate, it will encounter a number of predictable forces that will stand between it and change. Innovation blocks are associated with newsroom culture, processes, and physical assets that have become so embedded over time that they inhibit new ways of doing things. By identifying what blocks exist, specific strategies can be developed to overcome them. This theory was applied to three Canadian newspapers that had just gone through significant innovation projects. The research provides insight into what factors blocked each of these projects along specific strategies that were used to enable change.