Alongshore sediment bypassing rocky headlands remains understudied despite the importance of characterizing littoral processes for erosion abatement, beach management, and climate change adaptation. To address this gap, a numerical model sediment transport study was developed to identify controlling factors and mechanisms for sediment headland bypassing potential. Four idealized headlands were designed to investigate sediment flux around the headlands using the process-based hydrodynamic model Delft-3D and spectral wave model SWAN. The 120 simulations explored morphologies, substrate compositions, sediment grain sizes, and physical forcings (i.e., tides, currents, and waves) commonly observed in natural settings. A generalized analytical framework based on flow disruption and sediment volume was used to refine which factors and conditions were more useful to address sediment bypassing. A bypassing parameter was developed for alongshore sediment flux between upstream and downstream cross-shore transects to determine the degree of blockage by a headland. The shape of the headland heavily influenced the fate of the sediment by changing the local angle between the shore and the incident waves, with oblique large waves generating the most flux. All headlands may allow sediment flux, although larger ones blocked sediment more effectively, promoting their ability to be littoral cell boundaries. The controlling factors on sediment bypassing were determined to be wave angle, size, and shape of the headland, and sediment grain size.