Objective: The primary objective was to analyze percutaneous dilatation tracheostomy (PDT) management in the intensive care unit (ICU) by comparison with surgical tracheostomy (ST) outside of the ICU, with respect to: (i) long-term postoperative outcomes, including rate of follow-up, return to the emergency department, and major and minor complications; (ii) timing of decannulation, including time to decannulation, decannulation after >30 days, and decannulation at discharge. The secondary objective was to compare perioperative outcomes, including major and minor complications. Methods: A retrospective study from April 2013 to 2024 at a tertiary referral center. Eligible patients included those over 18 years old without PDT contraindications who received PDT in the ICU or ST. Results: Final analysis included 250 patients (125 [50%] PDT; 125 [50%] ST). The mean (SD) age of patients was 60.05 (16.41) years, and 85 (34.0%) were female. Compared with the ST group, the PDT group experienced significantly decreased long-term follow-up (41 [39.8%] vs. 115 [95.0%], respectively, p < 0.001), increased emergency department returns (61 [64.2%] vs. 31 [26.1%], p < 0.001), longer time to decannulation (estimated median difference: 11.00 days [95% CI: 7.00 to 15.00, p < 0.001]), increased decannulation after >30 days (23 [34.8%] vs. 13 [12.7%], p < 0.001), and similar postoperative complications (8 [8.4%] vs. 8 [6.8%], p = 0.664). The PDT group experienced significantly more perioperative complications (37 [30.1%] vs. 22 [17.6%], p = 0.021). Conclusion: The decreased long-term follow-up, delayed decannulation, and increased complications after PDT highlight potential pitfalls in ICU tracheostomy management, demonstrating the need for refined protocols, appropriate consultant involvement, and improved patient selection. Level of Evidence: 3 Laryngoscope, 2025