In agreement with Winnicott, the author considers all forms of playing as a place of transit between inner and outer reality and between unsymbolized and symbolized experience. Some forms of playing serve more exclusively to clarify the current state of the patient’s separate mind, while other forms of playing additionally introduce and mark forms of separateness between patient and analyst that are more likely to cause temporary disruption. This paper aims to distinguish between these two forms of play. Through clinical vignettes, the author demonstrates how each form of play offers various forms of containment, differing in the mechanisms of how to facilitate the process of metabolization. He also suggests that sometimes we can only know a posteriori of the patient’s experience of disruption and containment rendering these distinctions between types of playing as a rough scaffolding. Playing always implies a process that is in flux.