Small-caliber chest tubes are used to treat pneumothorax and pleural fluid collections. Although commonly considered a less invasive alternative to large-caliber thoracostomy tubes, small-caliber tubes have a high complication rate. Emergency physicians must be familiar with common and dangerous procedure complications associated with these devices and have a systematic and rapid approach to identify and solve malfunctions. Structured root cause analysis can facilitate identification of problems. We reviewed the medical literature for complications of small-caliber chest tubes and searched the U.S. Food and Drug Administration (FDA) database for complications of a specific pigtail catheter kit. Using a structured root cause analysis (RCA), we examined two cases of retained pigtail catheter obturators resulting in catheter malfunction and unresolved pneumothorax. We identified common complications of pigtail catheters from the medical literature, as well as 28 reports to FDA of complications with the kit used in the analyzed cases; ours were the only reports of the obturator error. RCA identified multiple contributing factors, including unrecognized and novel radiographic clues, human errors, communication breakdown, device design, and opportunities for improved systematic procedural approach. We discuss factors identified in RCA and regulatory considerations relevant to emergency physicians, including FDA reporting mechanisms. A structured review of complications of pigtail catheter insertion revealed opportunities for improved patient safety. We highlight a preventable error in insertion of a percutaneous catheter and describe radiographic features to enhance error detection. Improved design, systematic processes for device insertion and troubleshooting, and enhanced provider education could reduce the risk of medical device errors. An end-of-procedure time-out including instrument counts and systematic assessment of device function is a generalizable patient safety measure for bedside procedures.