This chapter aims to offer reflections from the authors’ participation in the Europe Engage project and their experiences of enacting service learning. It presents a series of common transnational considerations, contextual perspectives and barriers experienced in different European countries where service learning is embedded or beginning to take root. The chapter argues that awareness of challenges can enable more successful strategies and practices for sustainability. The adoption of pedagogical practices and models for different socio-political contexts need scrutiny and reflection in terms of potential benefits and limitations. In Europe, the term and the definition of service learning has been adopted from the United States and the English language. Developing data is a key to determining the impact of service learning in European higher education institutions. Service learning continues to grow in Europe, despite a lack of funds and national, local and institutional policies for supporting it.