There is a growing number of new digital technologies mediating the experiences of grief and the continuing bonds between the bereaved and their loved ones following death. One of the most recent technological developments is the “griefbot”. Based on the digital footprint of the deceased, griefbots allow two-way communication between mourners and the digital version of the dead through a conversational interface or chat. This paper explores the mediational role that griefbots might have in the grieving process vis-à-vis that of other digital technologies, such as social media services or digital memorials on the Internet. After briefly reviewing the new possibilities offered by the Internet in the way people relate with the dead, we delve into the particularities of griefbots, focusing on the two-way communication afforded by this technology and the sense of simulation derived from the virtual interaction between the living and the dead. Discussion leads us to emphasize that, while both the Internet and griefbots bring about a significant spatial and temporal expansion to the grief experience –affording a more direct way to communicate with the dead anywhere and at any time– they differ in that, unlike the socially shared virtual space between mourners and loved ones in most digital memorials, griefbots imply a private conversational space between the mourner and the deceased person. The paper concludes by pointing to some ethical issues that griefbots, as a profit-oriented afterlife industry, might raise for both mourners and the dead in our increasingly digital societies.