A lumen re-entry system includes a helically wound coil having an open proximal end and an open distal end and defining a longitudinal movement axis. The helically wound coil includes a relaxed distal segment that is relaxed relative to a proximal segment of the coil. A tip deflection wire is attached to the relaxed distal segment and coaxially disposed relative to the helically wound coil. Movement of the tip deflection wire in a proximal direction moves the lumen re-entry system from an advancement configuration in which the open distal end of the helically wound coil is substantially aligned with the longitudinal movement axis to a deflected configuration in which the open distal end of the helically wound coil is deflected relative to the longitudinal movement axis. The lumen re-entry system also includes a puncture wire slidably received within the helically wound coil and having a distal puncture tip.