Customer education or the extent to which firms are seen as providing customers with the skills and abilities to utilize critical information is often considered a valuable augmentation to a firm’s service offerings. Yet, many firms are hesitant to invest in customer education efforts for fear that it will equip customers with the skills to shop around and possibly switch providers. The purpose of this research is to understand the circumstances under which customer education ties customers more closely to a firm or encourages customers to leave. Specifically, our studies show that an understanding of this paradox of customer education lies in the specificity of customer expertise that is built as a result of customer education initiatives. The results demonstrate that educating customers for firm-specific expertise leads to increased loyalty, while building market-related expertise may decrease customer loyalty. A critical practical implication of our findings therefore is the need for managers to understand the varying effects of enhancing customers’ firm-specific versus market-related expertise and to consider customer education initiatives proactively.