Because maximizing the learning of new material is a relevant concern for most individuals, understanding the specific processes involved could be beneficial for people of all ages. Both encoding and monitoring occur during the learning acquisition phase, yet monitoring accuracy and subsequent neural activation have been relatively ignored in the literature. The current research adapts a common metacognitive paradigm using Judgments of Learning (JOLs) to explore the neural differences in monitoring between younger (18-25) and older (65+) adults. Participants were asked to remember natural scenes and predict encoding success by providing a JOL response for each item. Participants were told to respond “will remember” if they believed they would remember that item on a later recognition memory test or “will forget” if they thought they would forget that item on a later recognition memory test. Actual memory performance was compared to predicted memory performance to provide a measure of monitoring accuracy. Individuals reported a JOL response for 150 intact (Easy) and 150 scrambled (Difficult) scenes while in a 3.0T fMRI scanner. Despite minimal differences in behavioral performance, there were several age-related neuroimaging findings of note. When compared to younger adults, older adults had decreases in medial temporal lobe (MTL) activation, as well as contralateral recruitment of the anterior cingulate. Most importantly, the present study also disambiguated structures related to encoding success (the right parahippocampus) and monitoring accuracy (the anterior cingulate). A novel account of neural structures that mediate monitoring is provided both across items varying in difficulty (Easy and Difficult) and across different age groups (Young and Old). Encoding and monitoring are important for learning acquisition and the present research provides the first account that successfully disambiguates the two processes. Results are discussed in reference to their educational implications on resource allocation during the learning of new material.