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This article describes the development of the Judgmental Self-Doubt Scale (JSDS), an individual difference measure of generalized mistrust of one’s judgment. Study 1 undertook the construction of the scale and demonstrated its high internal consistency. Studies 2 and 3 showed that greater judgmental self-doubt was associated, in anticipated ways, with a wide variety of personal dispositions. In Study 4, judgmental self-doubt was consistently associated with confidence in specific judgments concerning moral dilemmas, risk assessment, controversial societal issues, and societal parameters. In Study 5, the differential confidence of high and low self-doubters was greater following a task that required a difficult decision than it was following one that required an easy decision. The authors discuss ways in which doubt about one’s judgment, as assessed by the JSDS, is implicated in judgment-related behaviors and, more generally, in personality functioning.