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When the Jews gathered at the water gate in Jerusalem on Rosh Hashanah to hear Ezra and the Levites read them the Torah, they cried. Hearing the Torah read and explained made them realize how far they were from living up to God's expectations. Seeing as Rosh Hashanah is the day when all mankind is judged, one might expect penitent tears to be very appropriate as this is a powerful way to show God that you are ready to stop sinning and start living up to his expectations. Good intentions aside, Nehemiah, Ezra and the Levites admonished the crying Jews (Nehemiah 8):

ויאמר נחמיה הוא התרשתא ועזרא הכהן הספר והלוים המבינים את העם לכל העם היום קדש הוא ליהוה אלהיכם אל תתאבלו ואל תבכו כי בוכים כל העם כשמעם את דברי התורה ויאמר להם לכו אכלו משמנים ושתו ממתקים ושלחו מנות לאין נכון לו כי קדוש היום לאדנינו ואל תעצבו כי חדות יהוה היא מעזכם והלוים מחשים לכל העם לאמר הסו כי היום קדש ואל תעצבו

The leaders repeat the admonition against sadness three times, presumably because the temptation to cry was very great. Despite this ancient exhortation against crying on Rosh Hashanah, Hayyim Vital tells us that his teacher Isaac Luria cried a great deal during the Rosh Hashanah prayers. Vital further informs us that his teacher said that מי שאין בכי' נופלת עליו בימים האלו הוא הוראה שאין נשמתו הגונה ושלימה. This quotation from Luria of course might be limited to the days of repentance that follow Rosh Hashanah, but because the main focus of that paragraph is Rosh Hashanah specifically the plain sense suggests that Luria's intention was for Rosh Hashanah as well. The reader is left wondering whether Isaac Luria disagreed with Nehemiah and Ezra or whether there is a way to reconcile these differing views on how to observe Rosh Hashanah.

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Rav Ovadia Yosef Yichaveh Daas (2:69) and Rav Moshe Shternbuch in Teshuvos V'hanhogos (2:268) answers this question by saying that although you should not cry in a depressed or scared sense on Rosh Hashana if someone does so as the result of a natural emotion of enthusiasm and devotion then it is appropriate.

Without explicitly referring to the contradiction in the OPs question others also make similar distinctions depending on what is motivating the person to cry.

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  • Perhaps we might get an example of the 'others'
    – user19234
    Nov 27, 2022 at 3:01
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Rav Moshe Shternbuch in Teshuvot Vihanhagot 2:268 quotes both the opinion of the Vilna Gaon (Sefer Maaseh Rav 207) that it is forbidden to cry, and the Arizal (Baer Heitev 584) that it is a sign of a good neshama if you cry. The former refers to crying from gloom, the latter can be explained by a ma'amar I once learned in Sefer Ma'amarim 5691 (I think it was Tik'u Bachodesh but can't chazer it now):

All of life for most of us is our nefesh bahamis. That's who we are. Our nefesh Elokis is a background influence, and occasionally is able to break through. When it does so, we have lucid moments of strong, deep, emotional connection to Hashem. On Rosh Hashana, we get a tremendous amount of siata dishmaya with regards to this, our nefesh Elokis is able to awaken our nefesh bahamis to feel a strong, powerful connection to Hashem, and this is often expressed through powerful tears. The tears are hard to put into words, but certainly they are not coming from depression or gloom. It is a combination of love, awe, yearning, appreciating the magnitude of the day, and so much more. It is a moment when our nefesh Elokis shows us who we really are, behind the grubby, coarse guf.

It never lasts, it is never meant to. We are supposed to go back and try, over and over, to achieve even a drop of this in our tefillot under our own efforts. Like a bolt of lightning in a dark stormy journey, we are given a little flash of where we are supposed to go, once a year, so we can keep pushing through the darkness in the right direction.

Note: It says in The Baer Heitiv (684:3) says in the name of the Arizal that if one instinctively cries on Rosh Hashana, it is a sign that he is being judged at that moment!

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