On Elul
Source Sheet by Rabbi Janine Jankovitz
Kitzur Shulchan Arukh 128:1
[The days] from Rosh Chodesh Elul until after Yom Kippur, are days of Divine favor [and acceptance.] Even though throughout the entire year the Holy One, blessed be, accepts the repentance of those who return to Hashem wholeheartedly, nevertheless, these days are unexcelled and most suitable for repentance, because they are days of mercy and favor.
On Rosh Chodesh Elul, Moshe went up Mount Sinai to receive the Second Tablets; he remained there for forty days, and came down on the tenth day of Tishrei when the atonement was completed. From then on these days have been designated as days of Divine favor [and acceptance,] and the tenth day of Tishrei as Yom Kippur [Day of Atonement].
In most communities it is the custom to fast on the day before Rosh Chodesh Elul and to recite the prayers of Yom Kippur Katan [minor Yom Kippur], in order to be spiritually prepared for repentance. If Rosh Chodesh occurs on Shabbos, Yom Kippur Katan is held on the preceding Thursday.
The Ari (Rabbi Yitzchak Luria), of blessed memory, wrote, "If he did not lie in ambush but Hashem made it happen, then I will provide …" (Exodus 21:13) The initials of the words [ina le'yado vesamti lecha] form the acronym Elul, to indicate that this month is a favorable time for repentance to be accepted for the sins committed during the entire year. It also alludes to the fact that sins done inadvertently also require repentance during this month.
וַאֲשֶׁר֙ לֹ֣א צָדָ֔ה וְהָאֱלֹהִ֖ים אִנָּ֣ה לְיָד֑וֹ וְשַׂמְתִּ֤י לְךָ֙ מָק֔וֹם אֲשֶׁ֥ר יָנ֖וּס שָֽׁמָּה׃
If [a person] did so but not by design—it came about by an act of God—I will assign you a place to which they can flee.
The interpreters of allusions also commented (Deuteronomy 30:6):
"And Hashem your God will circumcise your heart and the heart of your children;"
וּמָ֨ל יהוה אֱלֹהֶ֛יךָ אֶת־לְבָבְךָ֖ וְאֶת־לְבַ֣ב זַרְעֶ֑ךָ לְאַהֲבָ֞ה אֶת־יהוה אֱלֹהֶ֛יךָ בְּכׇל־לְבָבְךָ֥ וּבְכׇל־נַפְשְׁךָ֖ לְמַ֥עַן חַיֶּֽיךָ׃
Then your God will open up your heart and the hearts of your offspring—to love your God with all your heart and soul, in order that you may live.
Also, the initials of Ani ledodi vedodi li, I am my Beloved's and my Beloved is mine, (Song of Songs 6:3) form the acronym Elul.
אֲנִ֤י לְדוֹדִי֙ וְדוֹדִ֣י לִ֔י
I am my beloved’s And my beloved is mine
Also, the initials of Ish lerei'eihu umatanos la'evyonim, One to another and gifts to the poor, (Esther 9:22) form the acronym Elul.
וּמִשְׁלֹ֤חַ מָנוֹת֙ אִ֣ישׁ לְרֵעֵ֔הוּ וּמַתָּנ֖וֹת לָֽאֶבְיֹנִֽים׃
[They were to observe them as days of feasting and merrymaking, ] and as an occasion for sending gifts to one another and presents to the poor.
These acronyms are an allusion to three things: Repentance, Prayer, and Charity which must be practiced zealously during this month:
"Hashem will circumcise etc." alludes to repentance
"I am my Beloved's etc." alludes to prayer, for prayer is the song of love
"One to another and gifts to the poor," alludes to charity