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The intent of this article is to further explore and review the concept of countertransference, in its various, most commonly accepted meanings in the psychoanalytic literature. Major clinical and theoretical developments in this concept began in the 1950s, and have found centrality and coherence in Bion’s theory of containment. A basic issue in the discussion on countertransference is whether, and up to what point, analysts should allow themselves to be modified by the impact of their patients’ projections. Freud, Klein, Rosenfeld, and Bion all underline the importance of an impartial, balanced, and unstressed quality of the analyst’s receptivity with regard to the patient’s mental state, as well as the transformative complexity implicit in “trying to know.” In fact, the disturbance that is sparked in the analyst by his interaction with the patient is now considered unavoidable and has increasingly emerged as a specific topic of study. The author uses clinical illustrations from her work with children and adults, as well as observations from everyday life experiences, to exemplify the way countertransference interacts with the ability to observe empathetically, often hindering and distorting it, but also potentially enriching its depth and breadth.