Background Laryngoceles are rare pathological air-filled dilatations of the laryngeal saccule. Approximately 8% of laryngoceles can become infected and pus-filled, forming laryngopyoceles, of which there have been only 64 reported cases from 1925 to 2019. If untreated, they can lead to life-threatening complications including airway obstruction and deep neck space sepsis. The generally accepted management of laryngopyoceles is surgical, but there are no consensus guidelines available. Case Presentation We present two cases of elderly patients (89- and 90-year-old) with laryngopyoceles who were successfully managed with endoscopic surgery. Both presented with acutely worsening airway symptoms on the background of progressive dysphonia. Fibreoptic nasal laryngoscopy showed large supraglottic masses/swellings, and they underwent emergent microlaryngoscopy and deroofing of an infected laryngocele. Airway management was shared between the ENT and anaesthetics teams. One patient had awake fibreoptic intubation, while the other was trialed with apnoeic/Optiflow and insertion of a microlaryngeal tube via operative laryngoscope, but required tracheostomy due to limited access. They recovered well in hospital with intravenous dexamethasone and antibiotics. Both patients were asymptomatic at one month follow-up, with no laryngocele recurrence on repeat FNE. Histopathology did not show any malignancy. Conclusion The rarity of laryngopyoceles highlights the importance of maintaining a high index of suspicion in patients presenting with signs of airway compromise or potential deep neck space infection. Suspected cases should usually undergo prompt CT and flexible nasal laryngoscopy evaluation, with early ENT referral. Consideration should also be given to the most suitable approach to managing the airway and surgical approach to drainage and excision. Early recognition and definitive management of laryngopyoceles are important to prevent potentially life-threatening complications.