Anxiety disorder diagnosis is a risk factor for alcohol use disorders (AUDs), but mechanisms of risk are not well understood. Studies show that anxious individuals receive greater negative reinforcement from alcohol when consumed prior to a stressor, but few studies have examined whether anxious individuals receive greater negative (or positive) reinforcement from alcohol in a general drinking context (i.e., no imminent stressor). Previous studies have also failed to examine possible moderating effects of specific drinking contexts (e.g., drinking in a group or alone). Finally, no studies have investigated mediating variables that might explain the relationship between anxiety and reinforcement from alcohol, such as physiological response to alcohol (e.g., cortisol response). Data for this study were drawn from a large alcohol administration study (N = 447) wherein participants were randomized to receive alcohol (target peak BAC: .08 g%) or placebo in one of four contexts: group simulated bar, solitary simulated bar, group sterile laboratory, solitary sterile laboratory. It was hypothesized that anxiety would be associated with positive subjective response (SR) under alcohol (above and beyond placebo), indicating stronger reinforcement from alcohol. It was also hypothesized that social and physical drinking context would moderate this relationship. Finally, it was hypothesized that anxiety would be associated with a blunted cortisol response to alcohol (compared to placebo) and this blunted cortisol response would be associated with stronger positive SR and weaker negative SR. Results showed that anxiety was not associated with positive SR in the full sample, but drinking context did moderate the anxiety/SR relationship in most cases (e.g., anxiety was significantly associated with positive SR (stimulation) under placebo in solitary contexts only). There was no evidence that cortisol response to alcohol mediated the relationship between anxiety and SR. This study provides evidence that anxious drinkers expect stronger positive reinforcement from alcohol in solitary contexts, which has implications for intervention (e.g., modification of existing interventions like expectancy challenge). Null findings regarding cortisol response suggest alcohol’s effect on cortisol response to stress (rather than cortisol response to alcohol consumption) may be more relevant for SR and drinking behavior among anxious individuals.