In this paper, the results of a recent study aimed at understanding the influence of orientation on high cycle fatigue properties and final fracture behavior of alloy steel Pyrowear 53 is presented and discussed. This alloy steel has noticeably improved strength, ductility, and toughness properties compared to other competing high strength alloy steels having a near similar chemical composition and processing history. Test specimens of this alloy steel were precision machined and conformed to the specifications detailed in the ASTM standards for tension testing and stress-controlled cyclic fatigue tests. Test specimens were prepared from both the longitudinal and transverse orientations of the as-provided alloy steel bar stock. The machined test specimens were deformed in cyclic fatigue over a range of maximum stress and under conditions of fully reversed loading, i.e., at a load ratio of −1, and the number of cycles-to-failure recorded. The specific influence of orientation on cyclic fatigue life of this alloy steel is presented. The fatigue fracture surfaces were examined in a scanning electron microscope to establish the macroscopic fracture mode and to characterize the intrinsic features on the fatigue fracture surfaces. The conjoint influence of microstructure, orientation, nature of loading, and maximum stress on cyclic fatigue life is discussed.