The social compensation hypothesis states that the internet primarily benefits individuals who feel uncomfortable communicating face-to-face. In the current research, we tested whether individuals higher in social anxiety use the internet as a compensatory social medium, and whether such use is associated with greater well-being. In Study 1, individuals higher in social anxiety reported greater feelings of comfort and self-disclosure when socializing online than less socially anxious individuals, but reported less self-disclosure when communicating face-to-face. However, in Study 2, social anxiety was associated with lower quality of life and higher depression most strongly for individuals who communicated frequently online. Our results suggest that, whereas social anxiety may be associated with using the internet as an alternative to face-to-face communication, such a strategy may result in poorer well-being.