The connection between digital literacy and the three core dimensions of psychological well-being is not yet well understood, and the evidence is controversial. We analyzed a sample of 2,314 individuals, aged 50 years and older, that participated in the English Longitudinal Study of Aging. Participants were clustered according to drivers of psychological well-being using Self-Organizing Maps. The resulting groups were subsequently studied separately using generalized estimating equations fitted on 2-year lagged repeated measures using three scales to capture the dimensions of well-being and Markov models. The clustering analysis suggested the existence of four different groups of participants. Statistical models found differences in the connection between internet use and psychological well-being depending on the group. The Markov models showed a clear association between internet use and the potential for transition among groups of the population characterized, among other things, by higher levels of psychological well-being.