The micro-degradation processes related to the ductile-brittle transition are crucial for revealing hydrogen embrittlement mechanisms. This study investigates the evolution and transition of hydrogen-assisted damages in notched duplex stainless steel using a combination of microstructural characterization, numerical simulations, and mechanistic models. The results show that the brittle area of the fracture surface increases rapidly with decreasing cathodic potential, accompanied by the fractography transition in a sequence of voids, voids mixed with quasi-cleavage, and quasi-cleavage. While hydrogen-assisted dislocation emission from the void surface and stress concentration at the phase boundary promote nanovoid growth, hydrogen-enhanced plasticity facilitates preferential void growth along the ferrite block. At higher hydrogen concentrations, ferrite cleavage cracking may originate from prolate voids and hydrogen-augmented Cottrell dislocation reactions, reducing plastic strain near the crack tip and hence diminishing the formation of vacancies as void nuclei. Previous studies have focused on the statistics of hydrogen's effect on void size. This work demonstrates the dislocation mechanism of hydrogen-assisted void growth and provides new insights into the development of micro-mechanism-based models to predict hydrogen embrittlement.