Judgments of learning (JOLs) reactivity refers to the finding that the mere solicitation of JOLs modifies subsequent memory performance. One theoretical explanation is the item-specific processing hypothesis, which posits that item-level JOLs redound to the benefit of later memory performance because they enhance item-specific processing. The current study was designed to test this account. We factorially manipulated the organization (blocked vs. randomized) of categorized lists and JOL condition (item-JOLs, list-JOLs, no-JOLs) between participants, and fit the dual-retrieval model to free recall data to pinpoint the underlying memory processes that were affected by JOL solicitation. Our results showed that item-level JOLs produced positive reactivity for randomized but not for blocked categorized lists. Moreover, we found that the positive JOL reactivity for randomized categorized lists was tied to a familiarity judgment process that is associated with gist processing, rather than to item-specific recollective processes. Thus, our results pose a challenge to the item-specific processing explanation of JOL reactivity. We argue that JOL reactivity is not restricted to item-specific processing; instead, whether JOLs predominantly engage participants with item-specific or relational processing depends on the interaction between learning stimuli and JOLs.