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4. When was the first Shemita observed?[1]
The counting of Shemita first began when the Jews entered Eretz Yisrael and settled the lands. This occurred 14 years after the entrance into Eretz Yisrael, as it took 7 years to conquest the land and another 7 to settle it. Hence, the first Shemita was only observed 21 years after entering Eretz Yisrael.
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[1] Rambam Shemita 10:2; Toras Kohanim Behar 1; Aruch Hashulchan Haasid 15:2; Encyclopedia Talmudit Vol. 2 p. 220
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