This paper treats the failure analysis of prestressing steel wires with different kinds of localised damage in the form of a surface defect (crack or notch) or as a mechanical action (transverse loads). From the microscopical point of view, the micromechanisms of fracture are shear dimples (associated with localised plasticity) in the case of the transverse loads and cleavage-like (related to a weakest-link fracture micromechanism) in the case of cracked wires. In the notched geometries the microscopic modes of fracture range from the ductile micro-void coalescence to the brittle cleavage, depending on the stress triaxiality in the vicinity of the notch tip. From the macroscopical point of view, fracture criteria are proposed as design criteria in damage tolerance analyses. The transverse load situation is solved by using an upper bound theorem of limit analysis in plasticity. The case of the cracked wire may be treated using fracture criteria in the framework of linear elastic fracture mechanics on the basis of a previous finite element computation of the stress intensity factor in the cracked cylinder. Notched geometries require the use of elastic-plastic fracture mechanics and numerical analysis of the stress-strain state at the failure situation. A fracture criterion is formulated on the basis of the critical value of the effective or equivalent stress in the Von Mises sense.