Purpose: The paper aims to investigate and describe the complex and dynamic dilemmas teachers are facing connected to students' net-based out-of-school activities. Design/methodology/approach: The authors draw on the notion of dilemmatic spaces when thematically analyzing focus group interviews conducted with 41 teachers at three lower secondary schools in Sweden. Findings: Two themes capture the teachers' dilemmas concerning their students' net-based out-of-school activities--negotiations of content and negotiations of professional identity. When teachers take part in professional discussions where dilemmatic spaces are recognized, rather than focusing on either being for or against digitalization, they are enabled to express a multifaceted view of professional identity. Research limitations/implications: This study is a starting point for further studies investigating how pedagogical and didactic decisions are made in a digital time. Practical implications: The findings are expected to be helpful to policymakers in understanding teachers' work. Also, teachers can be empowered by taking the departure in the findings and discussing how to handle dilemmas fruitfully. Originality/value: In a rapidly changing digital society, it is important to investigate what dilemmas teachers face in their work in order to learn from them. This study is a significant contribution.