This paper offers a fractographic and numerical study of hydrogen-plasticity interactions in the vicinity of a crack tip in a high-strength pearlitic steel subjected to previous cyclic (fatigue) precracking and posterior hydrogen-assisted cracking (HAC) under rising (monotonic) loading conditions. Experiments demonstrate that heavier cyclic preloading improves the HAC behaviour of the steel. Fractographic analysis shows that the microdamage produced by hydrogen is detectable through a specific microscopic topography: tearing topography surface or TTS. A high resolution numerical modelling is performed to reveal the elastoplastic stress-strain field in the vicinity of the crack tip subjected to cyclic preloading and subsequent monotonic loading up to the fracture instant in the HAC tests, and the calculated plastic zone extent is compared with the hydrogen-assisted microdamage region (TTS). Results demonstrate that the TTS depth has no relation with the active plastic zone dimension, i.e., with the size of the only region in which there is dislocation movement, so hydrogen transport cannot be attributed to dislocation dragging, but rather to random-walk lattice diffusion. It is, however, stress-assisted diffusion in which the hydrostatic stress field plays a relevant role. The beneficial effect of crack-tip plastic straining on HAC behaviour might be produced by the delay of hydrogen entry caused by residual compressive stresses and by the enhanced trapping of hydrogen as a consequence of the increase of dislocation density after cyclic plastic straining.