A subintimal recanalization catheter assembly for recanalizing a blood vessel having an occlusion in a lumen thereof. The catheter assembly includes a hub assembly, a catheter shaft including inner and outer tubular members extending distally from the hub assembly, and an expandable structure mounted on a distal portion of the catheter shaft which is configured to be actuated between a collapsed configuration and an expanded configuration by longitudinal movement of the inner tubular member relative to the outer tubular member. The catheter assembly is configured to be advanced into a subintimal space between adjacent tissue layers of a wall of the blood vessel to facilitate reentry into the blood vessel lumen by advancing a penetration member distally out of the lumen of the inner tubular member and through the tissue layer into the blood vessel lumen distal of the occlusion.