Laura D’Angelo’s “The Loaded Chamber” provides her beautiful illustrations of “improvisational role play” and “generative enactment,” among other concepts. Her paper serves as a wonderful platform for me to discuss and illustrate the evolution of my work relative to the idea of psychoanalytic play. Having written extensively on the topic of improvisation in close to 50 publications over the last two decades, I have reached the conclusion that while the idea of improvisation in psychoanalytic treatment is necessary, it is not sufficient. Discussing D’Angelo’s compelling clinical work with her patient Andrew corresponds closely with my discussion of this evolution.