The aftermath of complex trauma deeply impacts one's self-organization and interpersonal relationships, often resulting in clients who present to therapy with borderline characteristics and are typically labeled as difficult to treat. Further clinical complications with paranoid features may quickly place the therapist at a loss with respect to managing perceived and/or actual threats to client safety. Using psychodynamic theories, especially Kleinian understandings of psychosis and Winnicottian approaches to early disturbance and its impact on the emergence of self, this article provides a detailed case illustration that explores how a critical reflection of countertransference as “enactment,” “communication,” and “imagination” can help the therapist to understand the client's unconscious symbolic psychic struggles and to guide treatment selections in the therapy process.