There are a relatively large number of unexplored issues in treating severely neurotic, character-disordered patients. The defining characteristics of these patients are formulated in dynamic, structural, and object relational terms. A discussion of the masochistic character is presented to exemplify such features. It is suggested that treatment is an inescapable struggle due to the distinctly created transference-countertransference ambience wherein character resistances emerge as therapeutic stalemates. The milieus characterized by stagnation and chaos are examined in relation to clinical examples. Finally, three essential technical issues are considered in terms of therapists’ capacity to “hold” patients’ externalized material, use the countertransference, and sooner or later, interpret primitive defensive constellations and transferences.