Status of fruit that began growing between 1 Tishrei and 15 Shevat of the 7th and 8th years
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I'm asking about the difference between the period from Rosh Hashanah of the shemitah year and Rosh Hashanah of the ma'aser year, which is 15 Shevat. The new year for shemitah is 1 Tishrei, while the new year for ma'aserot from fruit is 15 Shevat (Tu BiShevat), as ruled by Beit Hillel. While the shemitah year starts on 1 Tishrei, we are still actually in the sixth ma'aser year (with the seventh year beginning only on 15 Shevat). If so, if a fruit begins to grow before 15 Shevat, do we need to separate ma'aser ani from it, as is the rule for sixth-year produce? On the other hand, from the research I've done, according to halachah during the shemitah year every fruit that begins to develop after 1 Tishrei will have kedushat shevi'it and thus exempt from ma'aser.
Practically speaking, the same question applies every year when the ma'aser sheni year switches to ma'aser ani, and vice-versa. The "problem" stems from the fact that the shemitah year period is not the same as the ma'aser year period, so it turns out that there is always a time during the year (from 1 Tishrei to 15 Shevat) where the shemitah cycle year is ahead of the ma'aser year.
The problem and the doubt exists only in the transition between the ma'aser year and the shemitah year. However in transitions between the ma'aser sheni and ma'aser ani years, there is no such issue. This is because for fruit, the transition between ma'aser years is always on 15 Shevat, so the transition to the ma'aser sheni or ma'aser ani year will always be on this date (and whatever fruit begins to develop from this point on will belong to the new ma'aser year). However, the problem and doubt exist in the transition between the shemitah year and the ma'aser year. While the new ma'aser year begins on 15 Shevat, the shemitah year begins on 1 Tishrei.
About the beginning of the shemitah year, all of the fruit that begins to develop after 1 Tishrei belongs to the shemitah year and should be treated as having kedushat shevi'it. They are not obligated in terumot and ma'aserot at all (albeit, the Rash holds that even during the shemitah year, the new year for fruit is 15 Shevat; we do not follow his opinion).
For fruit that began to develop after 1 Tishrei of the eighth year and before 15 Shevat, it seems that the new ma'aser year for fruit has not yet begun. For this reason, there are opinions that the sixth-year obligations apply to this fruit, so ma'aser ani should be separated. Others hold that the first-year obligations apply, so ma'aser sheni should be separated. The latter is the opinion of the Chazon Ish.
Bottom line: Fruits that began to develop between 1 Tishrei and 15 Shevat of the shemitah year have kedushat shevi'it.
Fruits that began to develop between 1 Tishrei and 15 Shevat of the eighth year: we separate ma'aser sheni and redeem them on a coin without a blessing; some say one should give as well ma'aser ani.
For a detailed explanation of this topic, see Shabbat Ha'aretz, 4 §8:7, §13:1; and Katif Shevi'it 72:12.