As the proportion of older adults increase, there is a need to investigate ways to promote healthy cognitive aging. There is growing interest in longitudinal studies examining the impact of regular musical activity on nonmusical cognitive functions, but the financial and logistical challenges of such studies greatly limits the amount of research on this topic, especially in older adults. To surmount these challenges and stimulate the pace of research in this area we present a novel technology-based method for conducting longitudinal studies of regular singing and song learning in older adults. This method uses a tablet based app (SingFit-R) that is given to participants to take home and used for singing a specified number of songs per day. Participants choose the songs they will sing and then follow a singing schedule created by the experimenter. The app records a variety of data each time a song is sung, including song name, date and time of singing, an audio recording of the singer’s voice, and the user-set volume levels of 2 mnemonic aids that facilitate song learning: a “guide singer” and “lyric coach” (the user reduces the volumes of these aids as a song is learned). By analyzing these data researchers can verify compliance and track song learning over the course of the study. We tested the feasibility of longitudinal research with SingFit-R in a 5-week study in which older adults sang 6 songs per day for 5 days per week. We examined measures of working memory and emotion regulation in this group before and after this intervention, and compared them to control groups that listened to music or had no musical activity. Based on measures of attrition, compliance, and enjoyment among users of the app, we conclude that this method is suitable for larger-scale studies on the cognitive impact of regular singing and song learning in older adults.