This paper is an attempt to further the conversation about the possibilities of dialogue with technology that Wegerif and Major have initiated. In their paper Wegerif and Major have argued that “constructive dialogue with technology is possible, even essential, and that this takes the form of opening a dialogic space” and they also “argue against Buber that dialogic spaces do not all take the same form, but that they take a multitude of forms depending, to a large extent, on the (...) mediating technology”. Reflecting on the paper by Wegerif and Major, the present paper attempts to highlight certain issues and possibilities for such a dialogue. In the first section of the paper, Wegerif and Major’s discussion of technology-mediated dialogue has been reflected upon. This is followed by a reflection on the possibility and challenges of engaging in a dialogue with technology as ‘other’ by referring to the case of a robot ‘Sophia’ getting citizenship in the Kingdom of Saudi Arabia. The third section discusses certain concerns regarding the interpretation of Buber’s idea of dialogue by Wegerif and Major. The conclusive section highlights some key aspects that need to be considered while reflecting on the possibility of dialogue with technology. (shrink)