Megahal Grandmommy is a chatbot program I trained as a surrogate for my real grandmother, who was recently diagnosed with Alzheimers. In a private performance over the course of a number of months I conversed with this program, airing thoughts and fears for her situation, discussing events in our lives, and exploring the space around this impending loss. In later stages of existence, the piece has been installed as a program for viewers to interact with, exploring and piecing together a narrative with the fragments hidden in the program’s replies. The chatbot technology was chosen for this project specifically because of its limitations–the dysfunctional and fractured conversation which it is capable of seemed a suitable analogy for the degradation of communication I expect with my grandmother as her situation progresses. This piece functioned as a cathartic unpacking, a rehearsal for loss, and an inscription of a very particular textual, interactive portrait–and it has provided entirely unexpected moments of humor and relief.