Processing of glass is indeed challenging owing to its chemical passivity; it is prone to cracking while processing through mechanical and thermal modes without appropriate strategies. Near-field microwave drilling is a thermal-ablation based material removal technique of generating high heat flux in the targeted area. Glasses tend to fail quite frequently during this processing owing to thermal stresses (shock). It was therefore important to develop suitable strategies to minimize cracking during this potentially pragmatic process for microdrilling. Accordingly, in the present work, an attempt was made to change the medium of the interface at the target drilling zone through application of seven different surface precursors to influence the local heat-flow characteristics. The cracking behavior of the soda lime glass during microwave drilling in a customized applicator under controlled power input (90–900 W) at 2.45 GHz was investigated. The heat was generated inside the applicator by creating a plasma sphere in the drilling zone through a metallic concentrator. The thermal shock on the glass specimen was found reduced by the combination of a good dielectric precursor and microwave concentration for hotspot formation, which in turn, reduces the cracking/crazing tendency. Trials were carried out while drilling holes on 1.2 mm thick glass plates at various duty cycles (DCs) to study the crack intensity and pattern. The near-field microwave drilling condition was also simulated to obtain the contours of the induced stresses. The results so obtained were compared with the cracking signatures of the experimental outputs; a good correlation could be obtained. It was found that both solid and liquid fluxes as precursor could be effective to control cracking during microwave drilling.