Voluntary disclosure decisions are ubiquitous and have been extensively studied in economics. We explore the role of individual differences in strategic anticipation—the tendency to think iteratively about others’ minds—in these decisions, focusing on the context of test-optional college admissions. Across three studies (n = 897), we examine how strategic anticipation affects both information senders (student advisors) and receivers (admissions evaluators). We find that information senders with higher strategic anticipation are more likely to consider correlated signals (such as GPA) when deciding whether to submit a score, and have lower thresholds to submit. Information receivers with higher strategic anticipation demonstrate greater skepticism towards non-submitted scores, particularly when they believe the information is withheld for strategic reasons. These findings contribute to our understanding of how observed behavior in voluntary disclosure situations may deviate from economic theory predictions, highlighting the importance of individual differences in strategic anticipation of others’ inferences.