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Henri Rey’s seminal work on borderline and psychotic patients who alternate between claustro- and agoraphobic anxieties led him to identify the claustro-agoraphobic dilemma, where borderline, narcissistic, and schizoid patients experience no place of safety. These patients are afraid of being trapped while inside their object and terrified of disintegration if they escape to the emptiness of outside space. Michael Feldman and John Steiner, both of whom knew and worked with Rey, are in dialogue about both personal remembrances of Rey as well as about Rey’s concepts and their profound influence: reparation, a spatial model of mind, a marsupial space as an intermediate locus where the “joey” or patient can mature in the mother’s body and attempt some outside excursion, and safeguarding access to the protection of the mother. Susan Finkelstein and Heinz Weiss pick up the conversation to further elucidate Rey’s complex and important insights about the claustro-agoraphobic dilemma.