Service-Learning (SL) is an experience that allows students to (a) participate in activities co-designed in partnership by universities and local organizations and (b) reflect on the service activity in such a way as to gain an enhanced sense of responsibility. These experiences represent significant ways to meet and experience real-world contexts for students. The COVID-19 pandemic required Higher Education Institutions to rethink and shift in-presence courses to online platforms. This transition included SL courses as well. This study aimed to explore the responsibility and democratic dimensions elicited by an extreme online Service-Learning (XE-SL) experience and the perceptions of engaging in exclusive online service activities with local communities during the COVID-19 Italian national quarantine. A qualitative driven mixed-method longitudinal approach was chosen to triangulate qualitative (reflexive journal) and quantitative (pre-post questionnaire) data from 20 university students. The findings shed a positive light on the capability of XE-SL to promote a sense of responsibility, civic engagement, and the acquirement of democratic and transferrable competencies, such as perspective-taking, adaptability, cultural background respect, global mindedness, teamwork, leadership, communication, creativity, and organizational competencies. Reflection, connection, and being agents of change for the community were perceived as the major assets of the XE-SL experience, while adapting face-to-face SL experiences to exclusively online activities evoked ambivalent feelings in students. The study suggests a rethinking of the design XE-SL and other forms of eSL with the inclusion of more structured interactive activities within community contexts to favor students’ sense of connection to the community organizations or NGOs.