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Suppose someone makes kiddush and distributes all the wine evenly to everyone at the table, including himself, in small cups; but there were enough people that no one person received/drank a cheekful. Would someone fulfill their mitzvah of kiddush after-the-fact (yotzei bedieved) this way?

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See Shulchan Aruch Orach Chayyim 271:14 with Mishnah Berurah (especially paragraph 73) where it is explained that bediā€™avad they fulfill their obligation of kiddush if they act in the way you have described.

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