Prospective memory also known as remembering to remember is the process of remembering to carry out future actions. The present study investigated age-related differences in the performance of two complex prospective memory tasks for 30 younger adults (M = 19.43, SD = 2.10) and 30 older adults (M = 66.87, SD = 3.25). The two tasks had the same constraints, but were framed within different contexts (i.e., taking medications or scheduling groups). Participants performed the tasks within a simulated week based on activities they perform as part of their weekly routine, and they were given 30 minutes to develop plans to help them remember the tasks. Older adults were as accurate as younger adults in developing their plans for both tasks, but made significantly more errors in carrying out the prospective tasks. Planning style was not directly predictive of performance for the group task. However, age-related differences in performance for the medication task were related to planning style such that age-related declines in performance were observed for older adults who used a planning style that did not provide adequate memory support (i.e., list layout with time cues). Moreover, participants of all ages with lower levels of planning experience were more likely to select this ineffective planning style. These findings provide evidence that age-related differences in prospective memory can be ameliorated through the use of a familiar task and the opportunity to develop plans to remember the task. However, if participants develop an ineffective plan they will show performance decrements.