Nowadays, parents face the challenge related to social media use problems of their children, as the internet and related technology is more advance than previous days. Nevertheless, the young generation is enthusiastic about digital technology. The paradox of internet use in young and older generations has a different meaning as it widens the digital literacy gap. This study aimed to explore digital monitoring on the experiences of 123 participants. They were divided into four focus groups based on the stages of family development i.e. a group of single and new couples (n = 54), a group of families with children aged 0-6 years (n = 24), a group of families with children aged 7-11 years (n = 26), and a group of families with children over 11 years old (n = 29). There were 17 participants actively giving their thoughts, feelings, and experiences to focus group discussions within two hours of conversations. Using the Grounded Theory method and MAXQDA assistance of the 2018 version, we categorized themes based on 571 code systems. The topics discussed were digital monitoring strategies, digital paradoxes, digital parenting, role synergy, experiential learning supported digitally, and privacy. The contribution of this research to digital monitoring theories is the exploration of participants' contextual experiences.