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In the wake of her analyst’s death in the summer of 2024, Dr. Frankfeldt turned to an unlikely companion—ChatGPT—to help her explore a dream of that loss, discovering in the process surprising depths of insight and self-understanding. The AI even offered some solace during a time when she felt that starting with a new analyst was unpalatable. At the same time, the difference between the intellectual insight provided by a machine versus what a human-to-human relationship has to offer also became unquestionably clear. The author was formerly a “proper” analyst who upheld and valued the frame that provides a safe holding environment for us and our patients. Is her using ChatGPT as an adjunct helper “sleeping with the enemy?” The field of psychoanalysis is in jeopardy now that free or cheap AI “therapy” apps have become ubiquitous. Is the analyst colluding with the erosion of the field? Why are people, even therapists, flocking to use “chatbots” for “therapy” in the first place? There are numerous reasons for this besides availability and affordability. The article unpacks the allure of AI “therapy” apps and both their usefulness and dangers.