During learning, a shift in processing often occurs with increased task experience, where initialslow, algorithmic processing proceeds into fast, retrieval-based processing. Older adults are slower than young adults in the rate at which this shift occurs, in part due a reluctance to use a retrieval strategy. The present research employed task materials that alleviate age-related differences in associative memory so that participants could rely on prior knowledge, or schematic support. The goal was to determine whether older adults’ retrieval reluctance is due to a general avoidance of using the retrieval strategy or to low confidence in their memory for unfamiliar task materials. Participants completed two learning tasks: the Noun-Pair Lookup Task, where task materials consist of unrelated noun pairs, and an isomorph, the Grocery-Price Look Task, where task materials were grocery-items and prices. In this second task, the prices were either market-priced and consistent with everyday experience or were overpriced. Older adults were retrieval reluctant in the Noun-Pair Lookup Task, replicating previous findings. Stark condition differences were found in the Grocery-Price Lookup Task; older adults shifted much sooner for market-priced materials than for overpriced materials, and young adults shifted much later than expected for overpriced materials, where their final levels of learning were inconsistent with their memory use. Condition differences in retrieval use were substantially larger than the differences in retrieval accuracy. These results imply that confidence in using the retrieval strategy matters for both young and older adults, and that retrieval reluctance is not solely an age-related phenomenon.