When people rely on the web to gather and distribute information, they can build a sense of trust in the websites with which they interact. Understanding the correlates of trust in most websites (general website trust) and trust in websites that one frequently visits (familiar website trust) is crucial for constructing better models of risk perception and online behavior. We conducted an online survey of active Internet users and examined the associations between the two types of web trust and several independent factors: information technology competence, adverse online events, and general dispositions to be trusting or cautious of others. Using a series of nested ordered logistic regression models, we find positive associations between general trust, general caution, and the two types of web trust. The positive effect of information technology competence erases the effect of general caution for general website trust but not for familiar website trust, providing evidence that general trust and self-reported competence are stronger associates of general website trust than broad attitudes about prudence. Finally, the experience of an adverse online event has a strong, negative association with general website trust, but not with familiar website trust. We discuss several implications for online behavior and suggest website policies that can help users make informed decisions about interacting with potentially risky websites.