The aim of the present study was to test if a cognitive strategy improves older adults' prospective memory performance in a naturalistic health task. Moreover, it was tested if a possible strategy effect is moderated by individual differences. Therefore, a group of older adults was asked to perform a task taken from the medication adherence literature (i.e., blood pressure monitoring). Half of them were asked to form implementation intentions. Additionally, crystallized pragmatics and fluid mechanics, conscientiousness, self-efficacy, and lifestyle factors were assessed as possible moderators. Results showed a strong positive strategy effect on prospective memory. Moreover, the effect was qualified by a significant interaction and only emerged for participants with low levels in fluid mechanics. No other moderator showed an effect. In conclusion, an enhancing effect of implementation intentions on prospective memory seems to be dependent on individual differences in cognitive capacity and less related to key motivational or personality variables.