Since the introduction of the retrograde technique, the success rate of chronic total occlusion (CTO) percutaneous coronary intervention (PCI) has increased significantly in patients with suitable anatomy. To our knowledge, retrograde recanalization of a CTO from the abluminal side of a previously placed stent has not been reported. We describe a case of retrograde PCI of a mid left anterior descending (LAD) artery CTO through a previously placed proximal LAD stent which extended into the diagonal artery. The occluded mid LAD was recanalized using the retrograde approach in which retrograde wire crossing into the proximal LAD was successful only after high pressure balloon expansion of the previously placed proximal LAD-to-diagonal stent. Intravascular ultrasound imaging was also used to confirm an intraluminal location of the retrograde guidewire.