This paper is the first attempt to systematically apply Value Sensitive Design to social media. Moving from the claim that social media are morally relevant technologies, the paper aims to demonstrate their interactional nature and to provide a working definition of them as “communicative environments that allow a scalable sociality.” Both anthropological and ontological evidence are provided to support this purpose. The interactional stance allows social media to be designed according to the principles of built-in values and the VSD approach. After stating the VSD principles, a deeper investigation of its moral foundations is conducted. It is observed that while VSD sustains universal values, it does not give a sufficient rationale for them. The paper aims to provide a more robust foundation by integrating VSD with the moral imagination theo ry. This also permits revising the overall conceptual investigation of VSD and developing some specific tools for social media design. Finally, the moral relevance of social media is reconfirmed, given that they are conceived as imaginative technologies with a moral impact on their users’ lives.