Highlights Quantified particle size and shapes generated during hammer milling of softwood and wheat straw. Size reductions in length and width correlated with milling energy requirement. Assessed the validity of existing comminution laws for predicting milling energy requirement. Improved milling energy requirement prediction for softwood based on size reductions. Abstract. The valorization of agricultural and woody residues into higher quality fuels is an attractive pathway and can contribute to decarbonizing the energy system. One essential step for the conversion of these residues to fuels is comminution through commercial mills. This study aimed to investigate the effects of feedstock, input feed size, and milling screen size on particle size and shape, as well as to validate the reliability of existing comminution laws for predicting energy requirements during hammer milling of agricultural and wood biomass. Additionally, the study proposed a new empirical correlation for comminution energy prediction, taking two-dimensional size reduction descriptors into consideration. A machine vision-based image processing method was used to estimate particle size, particle size distribution (PSD), and particle shape factors. The aspect ratio of wheat straw particles was 1.3 to 1.5 times larger than softwood particles, suggesting they are more fibrous. The shapes generated during hammer milling were estimated, with rectangular shapes being predominant. The specific energy requirement (SER) estimated for the hammer milling of softwood chips and wheat straw at different mill screen sizes (4, 8, and 12 mm) was found to be in the range of 153.2–25.5 kJ kg-1 and 38.5–16.1 kJ kg-1, respectively. The validity of existing comminution laws to predict the SER during hammer milling of softwood and wheat straw was tested at a fixed feed rate of 45 kg hr-1, and an improvement in SER prediction for softwood was achieved by formulating a new empirical correlation factoring size reductions in length and width. Further, the correlation developed for the SER for wheat straw was found to lack statistical significance. The findings of this study can be applied to improve the effectiveness of the comminution process, a critical precursor to numerous thermochemical conversion methods used for transforming biomass residues into valuable fuels. Keywords: Bioenergy, Biomass comminution, Machine-vision image analysis, Particle shape, Particle size distribution, Specific energy consumption.