Today’s social and political movements against dominant Western narratives call for a re-contextualization of cultural heritage (CH) toward inclusivity, multiperspectivity, and sensemaking. Our work approaches this challenge from a Human–Computer Interaction (HCI) perspective, questioning how HCI approaches, tools and methods can contribute to CH re-contextualization. Through collaborative reflection on our research practice, we identified four diverging case studies highlighting the different roles of HCI and its increasing entanglement with CH. Case studies 1–3 focus on HCI as a medium for CH, case 4 on digital CH, and thereby on the HCI–CH entanglement. Our reflections contribute to CH re-contextualization by highlighting the need for co-design and slow design approaches, the role of HCI technologies in preserving, communicating, and shaping CH, and open questions and challenges related to the increasing HCI–CH convergence.