Abrasive grains and the associated bonding agent are the two significant components in the manufacturing of fixed abrasive machining tools. The material properties and interfacial bonding behavior between the grains and the bonding matrix determine machining performance. In precision machining processes with diamond abrasives, the primary failure modes of fixed abrasive tools are grain dislodgement and premature loss, leading to abrupt change in machining load and ultimately causing inaccurate and inefficient machining performance. This study develops a comprehensive model for understanding abrasive grain retention and interfacial failure mechanisms in resin-bonded diamond tools. Finite element analysis of a single diamond grain embedded in a resin matrix was conducted to examine the influence of the grain shape, protruding height, and orientation angle on critical interfacial failure force. A series of single diamond scratching experiments validated the model, revealing that the maximum retention force reached 43.56 N for grains with a 0.9 mm protruding height and a 60° orientation angle. The results also show that, within a specific grain size range, grain shape—quantified by the sphere deviation coefficient proposed in this paper, has the greatest impact on retention and failure behavior. Protruding height plays a secondary role, while the contribution of orientation angle is minimal. These findings provide valuable insights for the design, manufacture, and optimization of precision abrasive machining tools, particularly for applications requiring high precision and reliability.