This paper examines whether Catch-22 situations persist as equilibrium phenomena based on Gatekeepers' preferences rather than arbitrary rules. We model a game-theoretic scenario inspired by Heller's paradox, featuring a Requester (either Sane or Insane) who signals before a Gatekeeper decides to grant or deny their request. Our analysis identifies conditions where Catch-22 situations emerge as equilibria and evaluates their efficiency properties. Results demonstrate that such situations can arise naturally as efficient responses by Gatekeepers facing asymmetric information. The model is extended to labor markets, where "experience required for jobs, but jobs required for experience" creates similar dynamics.