Age-related episodic memory deficits imply that older and younger adults differentially retrieve and monitor contextual features that indicate the source of studied information. Such differences have been shown in subjective reports during recognition and cued recall as well as process estimates derived from computational models of free recall organisation. The present study extends the subject report method to free recall to characterise age differences in context retrieval and monitoring, and to test assumptions from a context-based computational model. Older and younger adults studied two lists of semantically related words and then recalled from only the first or second list. After each recall, participants indicated their subjective context retrieval using remember/know judgments. Compared to younger adults, older adults showed lower recall accuracy and subjective reports of context retrieval (i.e., remember judgments) that were less specific to correct recalls. These differences appeared after first-recall attempts. Recall functions conditioned on serial positions were more continual across correct recalls from target lists and intrusions from non-target lists for older than younger adults. Together with other analyses of context retrieval and monitoring reported here, these findings suggest that older adults retrieved context less distinctively across the recall period, leading to greater perceived similarity for temporally contiguous lists.