Many widely used numerical models of rock fracture based on mesoscale laboratory test characterisation of effective ‘intact’ strength parameters neglect microstructure effects. They therefore cannot explain grain boundary and pore effects on crack propagation and consequently are inadequate for models of rock destruction that exploit point and indentation stresses. Understanding deep drilling processes involving drill-bit buttons and/or water-jetting where rock loading is concentrated in domains with fewer mineral grains will therefore require models with microstructure. To investigate microscale failure mechanisms of granular rocks in diverse scenarios, we target a porous sandstone and introduce a novel workflow consisting of a computerized tomography (CT) based microstructure construction approach and a complementary mechanical numerical approach. The construction approach extracts the realistic rock microstructure and transforms the large voxel number CT-scan data into significantly fewer triangular elements. The finite-discrete element method (FDEM) with grain-based model (GBM) is adopted to solve the mechanics. The microscale failure mechanism of sandstone during the Brazilian test was thoroughly analysed using the numerical results together with the post failure CT-scan test data. The build-up of compressive and tensile stress chains, micro-crack nucleation, local relaxation, chain switching and final crack-path development exploiting pores was illustrated, revealing the micro-to-macro failure mechanism in time and space. Fracture paths in the specimens during Brazilian tensile test were dominated by the pores and the inter-grain boundaries. The tensile strength of the inter-grain joints was estimated to be at least 3.67 times the mesoscale specimen's intact tensile strength, while the pores account for 72.76% of the fracture path. The influence of the cementation distribution and microscale discontinuities was investigated with numerical cases.