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Character development does not end in childhood. It is a lifelong endeavor in which the undertaking of parenthood is a developmental stage. Parenting presents various challenges that promote maturation of the adult, while securing autonomy of the child. These adult developmental tasks include some that enhance abilities: respecting difference, accepting defiance, enduring anger, managing separations, and establishing identification with the child. In addition there are tasks that involve loss: relinquishing fantasies, tolerating disappointment, releasing the archaic bond, surrendering the helm, and withstanding one’s own abandonment. When the adult is incapable of successfully transiting through these parenting challenges, the child’s early ties to the primary caregiver are at risk of being abnormally extended. Parental refusal to relinquish the archaic attachment scuttles their offspring’s journey toward independence, and is referred to as “tethered love.” The concept of tethered love posits a pathogenesis of exaggerated compliance (or defiance) in children that begins with adult developmental failures in their caregivers. Clinical examples are used to underscore the suffocating impact of tethered love and demonstrate how the therapist must put aside feelings of distaste to better understand the child’s continuing connection to a constraining, even crippling, but often intensely loving parent.