There is a developing dialogue between the psychoanalytic and psychedelic fields of psychotherapy. This paper contributes to this emerging collaboration by applying Winnicott's concept of transitional experience to psychedelic clinical work. By analyzing two Ketamine-Assisted Psychotherapy (KAP) cases, we explore in depth how transitional experience facilitates psychedelic transformation. We review clinical touch and introduce hand-holding as a transformational experience that can occur in the amplified relational field of the psychedelic space. Applying these ideas will deepen clinicians' theoretical understanding and experiential practice of KAP.