A wire hoisting rope on a drilling rig failed during a lift, after a few cycles of operation, causing extensive damage to support structures. The failure investigation that followed included mechanical property testing and chemical, metallurgical, and finite element analysis. The rope was made from multiple strands of 1095 steel wire. Its chemical composition, ferrite-pearlite structure, and high hardness indicate that the wire is a type of extra improved plow steel (EEIPS grade). The morphologies of the fracture surfaces suggest that the wires were subjected to tensile overloading. This was confirmed by finite element analysis, which also revealed compressive contact stresses between the wires and between the rope and sheave surface. Based on the results, it was concluded that a tensile overload, due to the combined effect of a sudden load and undersized sheave, is what ultimately caused the rope to fail.