Abstract: A ladder stabilizing apparatus comprises a rail mount attachable to a ladder side rail and an auto-retracting belt assembly. The belt assembly comprises a rail interface connectable to the rail mount, a belt housing rotatable relative to the rail interface about a belt housing rotation axis, and a stabilizing belt extending from a belt first end to a belt second end. The belt first end is connected to the belt housing. The stabilizing belt is movable between a belt retracted position, in which the stabilizing belt is substantially wound within the belt housing, and a belt extended position, in which the stabilizing belt is at least partially unwound from the belt housing. The stabilizing belt is biased to the belt retracted position. The belt second end includes an environment anchor.