In this paper key seminal psychoanalytic theory is reviewed regarding the etiology and felt experience of those suffering from schizoid personality disorder. Particular attention is paid to the challenges and resistances to treatment experienced by both analyst and patient. The plight of two individuals is described. One is the case of an isolated, reclusive older man in treatment for many years and who was determined not to get well. The other is the account of a grandfather's efforts to reach a beloved grandson emotionally crippled and physically compromised by this disorder. Considerations for clinical practice based on these two cases will be discussed. Particular attention will be given to the analyst's awareness of the intense sensitivity of the schizoid person and the efforts needed to make and maintain a non-intrusive, non-controlling emotional resonance which allows the freedom for self- determined reintegration and maturational advance.