Postauricular cutaneous mastoid fistula secondary to chronic suppurative otitis media (CSOM) is an unusual complication. Bilateral manifestation along with primary acquired cholesteatoma and atelectasis of the pars tensa as an end-stage complication in the natural course of atticoantral CSOM is rare. This kind of complication has a very morbid effect on the ear, and it poses a therapeutic challenge in terms of eradicating disease and restoring function. In this article, we describe the unusual course of an atticoantral CSOM that (1) began as a primary acquired cholesteatoma simultaneously in both ears, (2) proceeded to automastoidectomy and a severe mixed hearing loss bilaterally, and (3) ended with the development of bilateral cutaneous mastoid fistulas that served to arrest the further progression of the disease process on its own. This case serves as a good demonstration of how a ventilating mastoid fistula can change the natural course of atticoantral CSOM and abort the occurrence of deadly complications.