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An herbaceous/grassy-like flavor has been reported by Chilean producers of Regina sweet cherry. There are no previous academic reports related to this flavor occurrence. Sweet cherries from five phenological stages were collected from six orchards with high herbaceous flavor incidence spanning Chilean production zones during the 2019/2020 season. Four experienced panelists tasted the fruit to identify the off-flavor incidence and intensity from four phenological stages, and the same cherries were analyzed for volatile compounds. Thirty-nine volatiles were identified and semi-quantified using solid-phase microextraction (SPME) and GC-MS. The highest off-flavor incidence was found at the bright red (stage 3) and mahogany colors (stage 4). No single volatile explained the herbaceous flavor consistently among orchards. However, it appeared that the off-flavor was related to delayed ripening in cherries, with more C6 aldehydes and less esters. Furthermore, rainfall and the elevation of the orchard had a significant effect on the incidence of off-flavor. Preharvest practices that promote fruit ripening along with avoiding early harvests are recommended to reduce the incidence of herbaceous flavor in Regina. [ABSTRACT FROM AUTHOR]