The current study explored factors influencing content sharing on Twitter in the context of sport news. It employed a 2-step text-based analysis combining qualitative and quantitative approaches and found that 3 main categories of factors are influencing retweeting decisions: characteristics of the source, characteristics of the message, and characteristics of the user. A subsequent hierarchical-regression analysis revealed that factors related to a user’s encounter of a Tweet are the best predictor of retweeting intentions. More specifically, interest in the exact topic of the tweet, the perceived relevance that the tweet might have for the user’s own followers, and similarity in opinion play important roles. Implications for communication practitioners, as well as research investigating human behavior on social media, are discussed.