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We present a case of a patient who presented for endocarditis and subsequently had a prolonged and challenging hospital course, with much of it spent in the intensive care unit (ICU). Throughout their hospitalization, personality factors, combined with impaired communication and pain in severe medical illness, led to challenging behaviors of disengagement, impulsivity, splitting, agitation, and suicidal statements. Experts in critical care psychiatry review the case and its key elements, including principles of critical care psychiatry and pharmacologic management of ICU patients; communication problems in ICU patients and associated psychiatric distress; the benefits of proactive consultation for challenging patients; and the construct of post-intensive care syndrome. Patients with personality disorders often struggle to cope with severe medical illness, leading to challenging, self-defeating behaviors. Such acts are even more difficult to manage in intensive care, where a patient’s tenuous medical status depends on smooth interactions between them and the medical team. We address how these challenges may be mitigated in collaboration with a psychiatric consult team.