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The consumption of garlic is inversely correlated with the progression of cardiovascular disease, although the responsible mechanisms remain unclear. Here we show that human RBCs convert garlic-derived organic polysulfides into hydrogen sulfide (H₂S), an endogenous cardioprotective vascular cell signaling molecule. This H₂S production, measured in real time by a novel polarographic H₂S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H₂S production from organic polysulfides is facilitated by allyl substituents and by increasing numbers of tethering sulfur atoms. Allyl-substituted polysulfides undergo nucleophilic substitution at the α carbon of the allyl substituent, thereby forming a hydropolysulfide (RS_nH), a key intermediate during the formation of H₂S. Organic polysulfides (R-S_n-R′; n > 2) also undergo …