Most studies have explored how information and communication technology (ICT) factors impact adolescents' schooling, but often ignore the potential influences on their well-being; no research has further scrutinized the moderating role of self-regulated learning (SRL) as a multi-dimensional combination, that is, different types of SRL learners. This cross-cultural study simultaneously scrutinized how distinct outside-of-school ICT factors influenced adolescents' digital reading and multi-dimensional well-being. It also took a person-centered approach to identify different types of SRL learners and examined whether the influences varied across the learner types. Data were based on 10,527 students in 308 schools from one East Asian region and one Western country participating in Programme for International Student Assessment (PISA) 2018. Multivariate multiple regression analysis revealed that overall, outside-of-school ICT factors impacted adolescents' digital reading and well-being differently, which also varied across cultures. Latent profile analysis detected culturally-mixed four profiles of SRL learners: High Profile (high in all indicators), Metacognitive Profile (in-between, optimal metacognition), Cognitive Profile (in-between, optimal cognition), and Low Profile (all low). It was the relatively weaker SRL learners in the East but the stronger SRL learners in the West that were particularly susceptible to the influences, either in a beneficial or detrimental way. Moreover, the cognitive, eudemonic, emotional and social dimensions of adolescents' well-being were all affected by ICT factors, without recurring trends in patterns. The findings provide implications to strictly monitor and guide adolescents' Internet use to enhance their academic and subjective well-being.