Some patients struggle with how they feel heard, seen, valued, judged, or ignored by the object. Guilt, anxiety, and control are major aspects of their daily life and can influence or shape the transference and countertransference. While making important progress in their treatment, patients can still struggle with these self and object conflicts. Using a contemporary Kleinian perspective, aspects of the interpretive process with such patients are explored, including how the role of transference and countertransference influences what we say. When deciding how, when, and what to interpret, the focus must include dynamics of transference, projective identification, containment, and the nature of unconscious conflict. With case material disguised for confidentiality, these elements are explored and the technical aspects of interpretation are demonstrated. The when, what, and how of interpretation are considered for cases with this more punitive and fragile image of the object and the view of the self as more aggressive or incompetent.