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The use of the empathic mode for engaging and communicating with patients has become widely accepted by many psychoanalytic psychotherapists since Kohut's early formulations (Kohut, 1971; Atwood & Stolorow, 2014). However, diagnostic understanding based on ongoing empathic immersion with our patients is often complicated because it is continually being modified as we know them more deeply and as transference and countertransference factors influence our perceptions. To illustrate the complexity of diagnosis when it is grounded in ongoing empathic engagement with our patients, I describe in detail my treatment of an elderly woman who initially presented with severe and acute symptoms of psychological, cognitive, and physical impairment. As the treatment has progressed, my diagnostic understanding has been continually modified to include a combination of psychodynamic and organic factors including PTSD, intense unresolved grief, and extreme feelings of guilt and need for punishment. Adding further to this conundrum, I have been frequently challenged by my own responses to the fluctuations in her progress, especially to periods of hopefulness followed by periods of despair and regression.