Elul - Teshuva Roadmap

[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 is He, accepts the repentance of those who return to Him 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 repentance¹The Scriptural verse referred to in the text deals with a homicide that was commited accidentally or inadvertently. during this month. The interpreters of allusions also commented: It is written (Deuteronomy 30:6) "And Hashem your God will circumcise your heart and the heart of your children;" the initials of the words [es levavecho ve'es levav] form the acronym Elul. Also, the initials of Ani ledodi vedodi li, ["I am my Beloved's and my Beloved is mine,"]²During these forty days, since repentance is more readily accepted, our repentance brings our hearts closer to our Beloved One and thus He, (our Beloved) is closer to us by accepting our repentance. (Mishnah Berurah preface to Chapter 581) [Song of Songs 6:3] form the acronym Elul. 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. 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.

.......Rabbi Yehoshua ben Karcha says, forty days did Moshe spend on the mountain - he read the doctrine of Scripture during the day and reviewed the doctrine of Scripture at night. And after forty days, he took the tablets and went down to the camp, and on the seventeenth of Tammuz he broke the tablets and killed the scorners of Israel. And he spent forty days in the camp, until he he burned the [golden] calf and ground it down like the dust of the earth, and killed all those who kissed the calf he expunged idol worship from Israel; and he set every tribe up in its place. And on Rosh Chodesh (the beginning of the month of) Elul, the Holy One, blessed be He, said to him (Exodus 24:12), "go up to Me to the mountain." And they blew the shofar (rams's horn) in the camp - since behold, Moshe went up to the mountain - such that they not err again after the worship of idols. And the Holy One, blessed be He, was exalted on that day with that shofar [blast], as it is stated (Psalms 47:6), "God is exalted by the shofar." And therefore, the Sages, ordained that we should blow the shofar on Rosh Chodesh Elul in each and every year....