Left main stem coronary perforation is a potentially fatal complication of percutaneous coronary intervention if not recognized early and treated emergently. Treating left main stem perforation can be challenging due to the significant hemodynamic effect of one of the important steps, namely balloon tamponade. Managing such perforation requires speed, precision, and a clear systematic approach to help save lives. We present a case of left main stem perforation that occurred during chronic total occlusion percutaneous coronary intervention which was treated with a covered stent across the left main stem into the left anterior descending artery. Restoration of flow into the circumflex was achieved by using a penetrating wire to cross into the circumflex, achieving hemostasis and preserving coronary flow into both epicardial coronary arteries. We describe further bailout strategies for dealing with left main stem perforations, including left main covered stenting with jailed side branch balloon and the simultaneous kissing stent technique.