This preliminary study examined the relationship between social anxiety and specificity of positive alcohol outcome expectancies (AOE) in a community sample of 62 drinking adults. The sample was divided into subsets of socially anxious (n = 17) and nonsocially anxious (n = 45) men and women. The Drinking Expectancy Questionnaire (DEQ) and Alcohol Expectancies in Social Evaluative Situations Scale (AESES) were used to determine if groups differed in the general positive AOE they hold, or only in AOE specific to social situations. ANOVAs revealed that socially anxious individuals had greater positive AOE specific to social situations (DEQ—Assertion scale and AESES) than nonsocially anxious individuals, with no differences in other positive AOE. Partial correlations controlling for social anxiety revealed that AOE specific to social situations correlated with greater drinking and alcohol dependency levels. Findings indicate that identification of AOE specific to social situations may be useful in classifying socially anxious individuals at risk for alcoholism and as a focus of expectancy challenge strategies for individuals with co-occurring social anxiety and drinking problems.