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Would it be permitted to set a cart with a sail in a reshus hayachid with the intent that if the wind picks up, it will carry the contents 1) into a reshus harabbim, or 2) through a reshus harabbim and into another reshus hayachid?

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Is there wind currently blowing? If not it would seem to only be a grama. – Double AA Apr 8 '13 at 2:42
Note also that if there is no hanacha in the reshus harabbim then it is not a biblical violation. – Double AA Apr 8 '13 at 2:43
Aaron, in light of @DoubleAA's previous comment, I would suggest you edit your question to refer to a case where the wind simply transfers the item from a reshus hayachid to a reshush harabim. – Michoel Apr 8 '13 at 2:45
The reason I chose to have it land in a reshus hayachid is that it seemed like it would be a more practically useful place for the contents to be, but I would be interested in either case. – Cislunar Apr 8 '13 at 2:49

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