© 2017 Wolters Kluwer Health, Inc. Objective The aim of this study was to evaluate screening questions for estimating nonsteroidal anti-inflammatory drug (NSAID) risk knowledge. Methods Cross-sectional data from a telephone interview of NSAID users 50 years or older from 39 physician practices in Alabama were used. Patient-reported awareness of prescription NSAID risk and health literacy were the independent variables, and a cumulative index score of objectively tested knowledge of 4 prominent NSAID risks was the dependent variable. General linearized latent and mixed model ordered logistic regression was used to estimate associations among the independent variables, covariates, and objectively tested NSAID risk knowledge. Population-averaged probabilities for levels of objectively tested NSAID risk knowledge were subsequently estimated. Results Subjective awareness of any prescription NSAID risk (adjusted odds ratio [AOR], 2.40; 95% confidence interval [CI], 1.55-3.74), adequate health literacy (AOR, 1.71; 95% CI, 1.04-2.83), and physician counseling about 1 or more NSAID risks (AOR, 1.69; 95% CI, 1.09-2.61) were significantly and positively associated with NSAID risk knowledge. The probability of correctly answering at least 1 of the 4 NSAID risk knowledge questions was 70% in the absence of any subjective risk awareness and in less than adequate health literacy. Whereas the probability of correctly answering at least 1 of the 4 NSAID risk knowledge questions increased to 86% in the presence of subjective awareness of any prescription NSAID risk and adequate health literacy. Conclusions Screening questions for subjective NSAID risk awareness and health literacy are predictive of objectively tested NSAID knowledge and can be used to triage patients as well as subsequently initiate and direct a conversation about NSAID risk.