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An experiment-informed discrete particle simulation study was performed to investigate the role of flexural particles in the shear flow of milled pine residues. Physical pine anatomical fraction samples were tested in an FT4 powder rheometer. A chip model for bark/stem chips and a fiber model for needles were proposed for DEM. The FT4 simulations show mixed fibers/chips require higher force and torque to drive shear flow than pure chips or fibers. The mass fraction and flexibility of fibers reveal nonlinear inter-dependency on impacting the shear flow of mixed fibers/chips. Polydisperse fibers well match the needle-rich samples on the flow attributes, while polydisperse mixed fibers/chips agree reasonably with the bark/stem-rich samples. The DEM study indicates that the flowability of pine residue biomass is determined collectively by various material attributes of the anatomical fractions, which must be considered when developing preprocessing methods for conversion-ready biomass with adequate material handling performance. [Display omitted] • Conducted dynamic shear flow test for pine anatomical fractions in an FT4 rheometer. • Developed DEM particle shape model strategy for mixed pine needles and woody chips. • Mixture of needles and chips are less flowable than pure needles and chips. • A specific set of needle mass fraction and flexibility exists for worst flowability. • Biomass flowability is governed by coupled effects of various material attributes. [ABSTRACT FROM AUTHOR]