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Why Are We Judged 3 different times about agriculture?
Good Yuntif.
I want to talk about a Mishna in the very beginning of Masechet Rosh Hashanah. It taks about when the different things in the world are judged.

(ב) בְּאַרְבָּעָה פְרָקִים הָעוֹלָם נִדּוֹן, בְּפֶסַח עַל הַתְּבוּאָה, בַּעֲצֶרֶת עַל פֵּרוֹת הָאִילָן, בְּרֹאשׁ הַשָּׁנָה כָּל בָּאֵי הָעוֹלָם עוֹבְרִין לְפָנָיו כִּבְנֵי מָרוֹן, שֶׁנֶּאֱמַר (תהלים לג) הַיּוֹצֵר יַחַד לִבָּם, הַמֵּבִין אֶל כָּל מַעֲשֵׂיהֶם. וּבֶחָג נִדּוֹנִין עַל הַמָּיִם:

(2) At four times of the year the world is judged: On Passover judgment is passed concerning grain; on Shavuot concerning fruits that grow on a tree; on Rosh HaShana, all creatures pass before Him like sheep [benei maron], as it is stated: “He Who fashions their hearts alike, Who considers all their deeds” (Psalms 33:15); and on the festival of Sukkot they are judged concerning water, i.e., the rainfall of the coming year.

but focusing on the shalosh regalim, there is a big question about this:
Why are we judged about different agricultural things on the Shalosh Regalim? and how does this connect to the chagim?
Let's go into greater detail about each one.

בְּפֶסַח עַל הַתְּבוּאָה

Pesach is when we are judged for the grain. it is easy to make, and it's easily and quickly made into something edible. This reflects well on Pesach, as the Jews left quickly and were made into a great nation right as they left.

בַּעֲצֶרֶת עַל פֵּרוֹת

Shavuos is when we are judged for the trees. and I think we can learn a valuable lesson from this. a tree takes a lot of work to nurture and grow, and over Sefiras ha'omer we have been trying to grow from our 'slavery' to matan torah.

וּבֶחָג נִדּוֹנִין עַל הַמָּיִם

And on Sukkot, we are judged in respect of rain. Sukkos is the holiday of huts. pretty ironic, as that's when we want the rain to come. there are many ways to connect sukkos to water. here are some -

1. simchas beis hashoeiva - public drawing of water from a well.

2. you can only use wet branches for the arba minim.

3. rain must be allowed to enter the sukkah.

and this is how we can connect them all to each other:
Agriculture holidays (the Shalosh Regalim) are times you might think "Look at all I did." you think "I accomplished so much."
but this is not the case. I think Hashem created the holidays connected to agriculture to remind us to instead say "Look at all Hashem did." and you think "Hashem accomplished so much for me."
We should always try to think "look at what Hashem did for me" instead of "look what I did."
Have a Good Yuntif!