Recent discoveries in the field of prospective memory (PM) show higher accuracy for remembering intentions in which prospective cue and action are strongly associated. In two experiments presented in this paper, participants encoded both high and low association cue–action pairs and were later tested on both prospective and retrospective PM components. Results of both studies show higher PM accuracy for the low association pairs, compared to high association ones, but only for the prospective component (across both Experiments) and only when a high association cue was presented first (Experiment 2). This finding was accompanied by longer study times for the low association pairs and study times were functionally related to later performance (across both Experiments). In the retrospective component, higher accuracy was observed for pairs with high level of association (but only in the first Experiment). Data are discussed in the context of metacognitive processes possibly related to the encoding of an intention as well as cue monitoring in case of PM tasks with high memory load and varying task difficulty.