Parenting children in the digital age involves the challenge of achieving the delicate balance between supervising children’s online behaviour and allowing them online independence. It can be even more pronounced in an insular culture based on Catholic values. This challenge is discussed in the view of the results of two studies, a qualitative study using focus groups with parents (n=26) and a survey questionnaire carried out to children aged 8 to 15 years and their parents (n=1,324). Results showed that there was a gap between what children do online and what their parents know about these practices. Parents have no clear-cut strategies to prevent risks. They use both enabling and restrictive mediation strategies, but the constant changes in technology mean that they have to adopt a “trial and error” approach to parenting.