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Why is it that we make Shehechiyanu both nights of Sukkos at candle lighting and Kiddush due to Sefeika DeYoma yet we only make Shehechiyanu on the Lulav on the first day?

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Because in theory you could have said Shehecheyanu when you prepared (bound) your lulav before Sukkos. So even supposing that the second day of Sukkos was the real Yom Tov (and the previous day was actually erev Sukkos), your Shehecheyanu then would still count as the real thing. (By contrast, with kiddush, you're saying the berachah because of the holiday itself - and conceivably it hadn't yet started the first night.)

(Mishnah Berurah 662:2, citing posekim)

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+1. But— but— You, of all people, are quoting the MB when the Baal Hatanya offers a different reason? ;-) – msh210♦ Oct 16 '11 at 7:29
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@msh: קבל את האמת ממי שאמרו, right? Anyway, I'm actually not aware of anyplace where the Alter Rebbe talks about this. Please enlighten me! – Alex Oct 16 '11 at 22:52
I don't know where, either, but someone told me in his name something like the following (which I may well be getting wrong or missing part of, which is why I'm not posting it as an answer): We treat the 's'feka d'yoma' day as yom tov for all k'dushas hayom purposes, so any shehecheyanu related to k'dushas hayom is repeated, but not the shehecheyanu on lulav which is a separate mitzva. – msh210♦ Oct 16 '11 at 23:38

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