Analytic writers have studied existential anxiety or annihilation anxiety, emanating from traumatic disruptions to people’s sense of going-on-being, reminders of their finitude, and facing a chaotic reality, and suggested that they can endure this anxiety by being with and living through it together with another person. The literature suggests that to be with patients who experience such anxiety, therapists need to indulge “narcissistically” in their own memories and fantasies of similar experiences, and, in parallel to the patients, enter transient regressive states. Sometimes, however, therapists are faced with a chaotic analytic reality that arouses existential anxiety in themselves, and seek to share it with their supervisors who, by experiencing parallel regressive states, can identify with their supervisees and grasp their experiences. Supervisors who consistently fail to be with their supervisees at such moments and persist in offering them new constructions of therapeutic materials might strengthen the supervisees’ defensive operations and disrupt their development as therapists.