Many models of professional self-regulation call upon individual practitioners to take responsibility both for identifying the limits of their own skills and for redressing their identified limits through continuing professional development activities. Despite these expectations, a considerable literature in the domain of self-assessment has questioned the ability of the self-regulating professional to enact this process effectively. In response, authors have recently suggested that the construction of self-assessment as represented in the self-regulation literature is, itself, problematic. In this paper we report a pair of studies that examine the relationship between self-assessment (a global judgment of one's ability in a particular domain) and self-monitoring (a moment-by-moment awareness of the likelihood that one maintains the skill/knowledge to act in a particular situation). These studies reveal that, despite poor correlations between performance and self-assessments (consistent with what is typically seen in the self-assessment literature), participant performance was strongly related to several measures of self-monitoring including: the decision to answer or defer responding to a question, the amount of time required to make that decision to answer or defer, and the confidence expressed in an answer when provided. This apparent divergence between poor overall self-assessment and effective self-monitoring is considered in terms of how the findings might inform our understanding of the cognitive mechanisms yielding both self-monitoring judgments and self-assessments and how that understanding might be used to better direct education and learning efforts.