A recanalization catheter for facilitating re-entry into a lumen of a blood vessel from a subintimal space. The recanalization catheter includes first and second mechanically actuatable wings positioned at a distal region of the elongate shaft of the catheter that are actuatable between a retracted position and an expanded position. In the retracted position the mechanically actuatable wings are positioned in first and second elongate channels defined in the elongate shaft, and in the expanded position the mechanically actuatable wings extend outward from the first and second elongate channels. The actuatable wings extend in an arcuate path away from the elongate shaft in the expanded position to be positionable in a circumferential orientation within a subintimal space formed in a vessel wall to automatically orient a lateral port of the elongate shaft toward the true lumen.