Climate change is driving phenological shifts worldwide, but key gaps remain in our understanding of the causes and consequences of these shifts. Here, I explore experimental, literature-based and model-based approaches to examine the causes and consequences of phenological shifts. Using experimental studies, I illustrate how phenograms, the phenology-ontogeny landscape, and dynamic food webs probe the consequences of phenology in a community context. Experiments manipulating seasonal timing reveal strong seasonal windows of opportunity and suggest a steep underlying fitness landscape associated with phenological shifts relative to the surrounding community. Using literature-based and simulation-based approaches, I show how graphical models of the environment-phenology relationship and the cue-strategy-fitness relationship can contribute to a more mechanistic understanding of phenological shifts and mis-matches. These studies suggest that a clear distinction between environmental (cue-driven) and organismal (response-driven) mechanisms could help resolve some persistent confusion in the field. Simulation studies suggest that variation in the evolution of phenological cueing strategies reflects differences in the quality of different cues in different locations. I contend that a mechanistic understanding of how environmental cues drive phenology and the evolution of phenological cueing strategies will be necessary to improve our ability to predict future phenological shifts in a community context.