Certain kinds of second analyses are destined to be difficult. The situation where a patient is compelled to leave a highly idealized analyst to seek another analyst's help is replete with opportunities for the patient to find the new analyst to be irretrievably disappointing. A powerful idealizing transference to the previous analyst can function to obscure and redirect feelings of abandonment and hostility. In addition, allowing a new, positive therapeutic alliance constitutes a threat to one's fidelity to the previous analytic experience, which may need to be protected at all costs. Three brief case examples illustrate how this dynamic can lead to a disrupted second analytic endeavor. Taking on a second analysis may require the new analyst to use a different approach, particularly when an idealizing transference in the first analytic relationship is interrupted in such a way that the development of another therapeutic alliance becomes an impossibility.