Devices, systems, and methods to generate a bypass lumen in connection with a chronic total occlusion procedure. An exemplary method comprises introducing at least part of a first elongated body into a lumen of an artery so that a distal tip of the first elongated body is positioned on a first side of an occlusion within the lumen of the artery; inserting the distal tip of the first elongated body into a wall of the artery in between a tunica media and a tunica intima of the artery; advancing the distal tip of the first elongated body in between the tunica media and the tunica intima; and further advancing the distal tip of the first elongated body back into the lumen of the artery to generate a bypass lumen and so that the distal tip is positioned on an opposite second side of the occlusion within the lumen.