Apparatus and associated methods relate to a distance-learning safety retraction device (DLSRD) mechanically coupled to a fixed anchor point on a boundary-mapped surface, the DLSRD including two receivers in operable communication with a transmitter borne on a user. In an illustrative example, the DLSRD may determine an angle between a lanyard coupled to the user and a vertical plane between the two receivers. The DLSRD may include, for example, an extraction detector detecting an extracted length of the lanyard. The DLSRD may determine user proximity to a safe operating area boundary based upon a difference of a current extracted length of the lanyard to a learned extracted length associated with a current angle of the lanyard, for example. Various DLSRDs may be configured in a run-mode to apply a braking effect to the lanyard and/or to activate a warning device based upon the user’s proximity to the boundary.