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The clinker grinding stage in Portland cement production is highly energy-intensive, primarily due to particle agglomeration and intensified interparticle attractive forces that hinder efficient comminution. Grinding aids (GAs) are routinely employed to mitigate these issues, enhancing grinding efficiency and improving cement performance. However, the undesirable side effects associated with conventional GAs on cementitious systems have spurred interest in modification strategies that can concurrently optimize grinding efficiency and final product quality. In this study, widely used commercial GAs, triisopropanolamine (TIPA), diisopropanolamine (DEIPA), and diethylene glycol (DEG), were chemically modified via esterification with organic acids of different carbon chain lengths. Cement specimens incorporating these modified GAs were produced at two dosages (0.05% and 0.1% by mass of clinker + gypsum), resulting in 24 distinct Portland cement formulations alongside a control mix. The influence of modification on grinding efficiency, particle size distribution (PSD), and powder flowability was investigated. Furthermore, scanning electron microscopy (SEM) was utilized to analyze particle morphology and concrete microstructural characteristics with powder flow behavior. The results indicate that organic acid modification not only facilitates achieving target fineness with lower energy consumption but also markedly improves both the PSD profile and the powder’s flow properties. Specifically, hexanoic acid-modified TIPA and DEIPA, along with propanoic acid-modified DEG, delivered the most favorable outcomes across the evaluated parameters. These findings underscore the potential of developing next-generation, modified GAs that simultaneously enhance energy efficiency and powder handling in cement grinding operations.