Florida Scrub‐Jays (Aphelocoma coerulescens) are cooperative breeders endemic to Florida’s oak scrub. In autumn, Florida Scrub‐Jays cache thousands of acorns and exhibit behaviors that appear to balance cache site selection against food degradation or cache robbery. However, both experience and position within a social dominance hierarchy could affect individual cache preferences. We examined the cache site preferences of birds with differing levels of caching experience and at different strata within a complex social dominance hierarchy. Our objective was to determine how experience, social position, and social context when caching influenced microhabitat preferences, and if these change as jays age, gain experience, and their social position changes. Naïve first‐year birds preferred to cache in well‐hidden, densely vegetated sites with relatively high soil moisture content. Naïve birds also cached farther from provisioning points if observed by a socially dominant bird than when they were alone or in the presence of birds of equal social status. Experienced adults preferred to cache in open, dry sandy sites and social context at the time of caching did not influence their preferences. As naïve birds aged, they gained experience and their social position changed. Experienced second‐year birds shifted their preference to more open, drier sites, and did so more often when they remained subordinate within their group rather than becoming dominant breeders. Second‐year birds that remained subordinate did not alter their caching behavior if observed by dominant birds. These patterns suggest that after gaining experience, jays learned which sites were more appropriate for caching and shifted their preference, regardless of their changing social status. We suggest that the risk of cache loss to food degradation might be greater than the risk of pilfering for Florida Scrub‐Jays, especially for birds in any social strata except the most subordinate, but this requires additional study.