Social media can be used to acquire online social support, and this online support appears to offer similar benefits to face-to-face social support. However, some research suggests that gaining this online support may increase the likelihood of developing a dependence on online platforms leading to addictive behaviors toward social media. Individual differences likely play a role in predicting who is most or least vulnerable to social media addiction, and the competing hypotheses of social enhancement (i.e., rich-get-richer) versus social compensation (i.e., poor-get-richer) help contextualize the use of social media, including addictive use. The present study explored the association between online social support and addictive use of social media, as well as the potential moderating roles of social anxiety and offline social support. Results showed that online social support was positively correlated with addictive use of social media, and social anxiety and offline social support significantly moderated the relationship between online social support and addictive use of social media. Results are discussed in relation to the “rich-get-richer” hypothesis, and implications regarding social anxiety and the importance of offline social support and clinical practice are considered.