A reentry catheter having a catheter body having a lumen extending axially through a length of the catheter body, a distal port in communication with the lumen, and a flexible distal tip positioned at a distal end of the catheter body. The distal tip can have a first planar surface and a second planar surface that are angled to form a tapered portion in the distal tip. A thickness of the tapered portion in a first direction can decrease along the length of the tapered portion and can be less than a width of the tapered portion in a second direction at every point along the length of the tapered portion such that the tapered portion of the tip is more flexible when bent in the first direction than in the second direction, the second direction being normal to the first direction.
