Emergency catheter cricothyroidotomy often fails. Case reports have concentrated on kinking and displacement of the catheter as the major causes. We investigated catheter tip penetration of the trachea. Using insertion angles of 90°, 75°, 60°, 45° and 30° we advanced 14 G intravenous catheters into fresh isolated sheep tracheas during high pressure oxygen insufflation. At all angles, the catheter tip became blocked by pushing into the mucosa with submucosal gas injection on one or more attempts. Full thickness rupture with extratracheal gas also occurred on insertions at 90° and 60°. We then tested a Luer-mounted prototype wire stylet which remains in situ during insufflation. Using the same methodology, the stylet was able to be placed and prevented blockage at all angles of insertion. Mucosal trauma and submucosal gas injection occurred on insertions at 90° and 75°. Our results should guide further stylet design.