Occasionally a patient comes along who is so frozen in an infantile state of disorganized attachment that the patient cannot take what the therapist is offering yet cannot leave the therapist either. Instead the two remain stuck in an unholy scenario of protracted destructive enactments, chronic mis-attunement, and rigid indigestible projective identifications. These seemingly impossible therapeutic encounters can include psychotic transferences, negative therapeutic reactions, or impasses. This article examines two such cases in detail and explores possible ways of understanding what failed in each of them and the impact of this on the therapist.