Highly processed foods tend to form weak structures which breakdown rapidly in the gastrointestinal (GI) tract, often causing negative effects on human metabolism and health. Developing healthier foods has been limited by the lack of understanding of how foods are digested. Through computational modelling we reveal mechanical gastric food breakdown phenomena and relate food mechanical properties with performance during critical initial digestion stages. Our model relies strictly on a viscoplastic-damage constitutive law, calibrated via rheological experiments on an artificial biscuit bolus and validated by simulating cutting tests. Simulations suggest that bolus separation during bolus backward extrusion and/or indentation by peristaltic waves, and, bolus agglomeration due to hydrostatic compression near the pylorus, are two competing phenomena that can influence the bolus free surface to volume ratio. This showcases the importance of including mechanical aspects of breakdown when designing foods for controlled chemo-mechanical breakdown and associated nutrient release rates.