The author describes a particularly perilous frontier on the psychoanalytic landscape—namely, the treatment of suicidal patients with serious personality disorders. Using a clinical example of egregious boundary violations by an analyst, he describes specific countertransference pitfalls that lead to mishandling the patients' expressions of suicidal despair. These include disidentification with the aggressor, failure of mentalization, collapse of the analytic play space, reactions to loss in the analyst's personal life, omnipotence, envy of the patient and masochistic surrender. The author emphasizes the unique vulnerabilities that accompany analytic treatment of such patients.