The quality of the therapeutic alliance is the foundation upon which all other therapeutic endeavors are based. While there are conditions that facilitate the development and maintenance of an effective therapeutic alliance (see Chapter 3), there are also conditions that militate against its development and maintenance. This chapter focuses on one set of these conditions, transference and countertransference, that can and do interfere with the therapeutic relationship as well as therapeutic outcomes. This chapter begins by describing transference, countertransference, and their enactments. Then it describes how transference and countertransference can be recognized and resolved. Finally, it illustrates how these enactments can be recognized and resolved in session transcriptions from two cases.