The popularity of Internet use brings more potential for healthy cognitive aging among older adults. Emerging studies have examined the age and gender differences in the link between older adults&rsquo; Internet use and cognition. However, few studies have investigated the gendered age difference regarding this association. The purpose of this study was to examine whether age would moderate the effect of Internet use on cognition among middle-aged and older adults and whether this relationship would be different between men and women. A total of 6,338 adults aged 50 or older were drawn on from the 2016 Wave of the Health and Retirement Study. Sequential linear regressions were conducted to examine the interactions between Internet use, age, and gender on cognition. The three-way interaction of Internet use, age, and gender was a significant predictor of cognition (&beta; = 0.01, p < 0.05). Specifically, the positive effect of Internet use on cognition was higher among older women of older age than those of younger age, while the positive effect remained the same for older men of different ages. The Internet offers a valuable resource for engaging middle-aged and older adults in activities that not only provide social interaction but also stimulate cognitive processes. The study suggests that the aging process does not necessarily inhibit the cognitive benefits that middle-aged and older adults can gain from using the Internet. Findings from this study indicated that future Internet/technology training to increase cognition among middle-aged and older adults should be age- and gender-tailored.