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Transference and countertransference forces in the lawyer-client relationship can interfere with the successful completion of the legal work the client retained the lawyer to perform. In such instances, a working knowledge of the concepts of transference and countertransference can aid lawyers in recognizing and managing these forces when they threaten to be disruptive. In more complex cases, a consultation with a psychoanalyst can be highly beneficial to the lawyer in understanding and working with the transferences and countertransferences at play. Two cases from an estate planning law practice are presented to illustrate transference-countertransference dynamics in the lawyer-client relationship as well as how psychoanalytic education and consultation can help lawyers avoid enactments that lead to stalemates and failures in legal practice.