Monitoring the environment for the occurrence of prospective memory (PM) targets is a resource-demanding process that produces cost to ongoing activities. The current study investigated younger and older adults’ ability to monitor strategically, which involves the heightening and relaxation of monitoring when it is contextually appropriate thereby affording conservation of limited-capacity attentional resources. Participants performed a lexical-decision task in which words or nonwords were presented in upper or lower locations of the screen. The specific condition was correctly informed that PM targets (“tor” syllable) would occur only in word trials (simple cue; Experiment 1), in word trials in the upper location (complex cue; Experiments 2 and 3A), or in red trials in the upper location (complex cue; Experiment 3B), whereas the nonspecific condition was told that targets could appear in any context. The results showed that older adults generally exhibited similar monitoring patterns as younger adults. When context varied randomly on each trial, younger and older adults in the specific condition utilized simple (Experiment 1) but not complex (Experiment 2) contextual cues to reduce monitoring in unexpected contexts relative to the nonspecific condition. Notably, younger but not older adults were able to use the location dimension of the complex cue to reduce monitoring in unexpected (lower) contexts. When context varied more predictably (i.e., changed every eight trials), both younger and older adults were able to monitor strategically in response to the complex contextual cue (Experiments 3A and 3B). Together these findings suggest that context-sensitive PM monitoring processes generally remain intact with increased age.