Self-defeating behaviors are present to some degree in every psychodynamic treatment. We will explore ways in which sadomasochism manifests, particularly in the transference/countertransference arena. The developmental roots and psychodynamic underpinnings will be illuminated through clinical examples. A contemporary understanding via Neuropsychoanalysis will explore self-defeating behavior as a problem with the PLAY instinct, leading to impairment in the ability to collaborate. The goal will be to fortify practitioners for what are often long and difficult treatments.