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Halogenated benzoquinones (HBQs) are frequently detected in tap water. HBQ levels are correlated with water age. As the water–transmission distance (water age) increases, the levels of bromo-benzoquinones (Br-BQs) decreased and those of chloro-benzoquinones (Cl-BQs) remained relatively stable in drinking water–distribution system in the presence of residual chlorine. 2,3,5,6-Tetrachloro-1,4-benzoquinone (TCBQ) and 2,6-dibromo-1,4-benzoquinone (DBBQ) were the most abundant Cl-BQ and Br-BQ, with maximum concentrations of 60.2 and 181.4 ng/L, respectively. TCBQ and DBBQ were chosen as representatives of HBQs to investigate their reactions with chlorine, including kinetics, pathways, and changes in toxicity. The hydrolysis and chlorination rates of HBQs were significantly pH-dependent, and the kinetic rates of DBBQ were faster than TCBQ in the pH range of 5–10. Chlorination converted highly toxic TCBQ and DBBQ to less-toxic chlorinated/brominated aliphatic disinfection by-products (DBPs), thereby reducing the overall toxicity of water bodies. This study provides comprehensive insights into the distinct life cycles of TCBQ and DBBQ in drinking water, covering formation, transformation, and toxicity. These findings provide a nuanced understanding of the risks posed by HBQs at various locations within the drinking water distribution system, offering valuable guidance for improving the control of DBPs in drinking water. [Display omitted] • Evolution of HBQs and aliphatic DBPs with age of drinking water was investigated. • Uncovering the reasons for the differ trends in the conversion of Cl-BQs and Br-BQs. • Formation and transformation mechanisms of HBQs were studied. • Chlorine conversion of HBQs reduced the toxicity of water samples. [ABSTRACT FROM AUTHOR]