Even though a variety of cognitive interventions have been conducted to ameliorate age-related cognitive declines, the effects of cognitive intervention using activities in everyday life are still unknown. The purpose of this study was to compare the effects between tablet computer-based productive and receptive cognitive engagement using an alternating-treatment design. Three healthy older adults performed a total of 19 sessions consisting of three baseline periods and 16 alternating training sessions. The training sessions were divided into four blocks and each block involved four treatment sessions. Productive and receptive engagements were randomly allocated to four treatment sessions. All participants alternatively received productive engagement that requires learning new practical applications and receptive engagement requiring little new learning such as listening to music. Prefrontal cortex (PFC) activity using functional near-infrared spectroscopy and executive function through the Trail Making Test were assessed at the baseline and the end of each session. All data were visually analyzed. Visual analysis results showed that the productive engagement was associated with higher PFC activity and faster performance in the Trail Making Test, compared to those utilizing receptive engagement. These results suggest that productive engagement might be effective in facilitating PFC activity and improving the executive function of healthy older adults, indicating cognitively challenging activities are more beneficial relative to nonchallenging activities.