Aims: To review cases of post-tracheostomy stenosis (PTS) following routine surgical tracheostomy in head and neck patients, outline management challenges, and identify documentation gaps that limit understanding of surgical risk factors. A literature review was also undertaken to identify potential surgical contributors to PTS, and a standardised documentation framework is proposed to support effective audit and future research. Methodology: A retrospective review was conducted of patients who developed symptomatic PTS after surgical tracheostomy at the Royal Brisbane and Women’s Hospital in 2024. Demographic data, surgical details, clinical presentation, interventions, and outcomes were collected through November 2025. Results: Four patients aged 60–84 years developed symptomatic PTS after temporary surgical tracheostomy performed for head and neck cancer surgery or airway obstruction. All initially recovered well and were decannulated before re-presenting with airway compromise. Management included emergent laryngoscopy with steroid injection, balloon dilatation, cryoablation, reinsertion of a tracheostomy tube, and in one case cricotracheal resection with primary anastomosis. Three patients achieved sustained airway patency and remained decannulated at follow-up. One patient who declined further intervention received palliative care and died from respiratory failure. Conclusion: PTS is an uncommon but clinically significant complication following temporary surgical tracheostomy and often requires multiple airway procedures. Current literature provides insufficient consensus on surgical techniques to prevent PTS, and limited operative documentation in our cases hindered identification of modifiable risk factors. A standardised tracheostomy documentation framework, such as the one proposed, may enable more robust audit, multicentre research, and future improvements in the prevention of PTS.