The month of Elul is referred to as the month of Rahamim and Selihoth (mercy and forgiveness). The roots for this can be found at the time when the Children of Israel travelled in the desert and with the sin of the golden calf.
When Moshe Rabbenu (Moses) 'a"h, descended on the 17th of Tammuz with the Luhoth (tablets of stone) and witnessed the terrible sin of the golden calf, he broke the Luhoth. G-d, in His wrath (over the Children of Israel's transgression) wanted to eradicate the Jewish people, continuing their existence through the seed of Moshe Rabbenu, 'a"h, alone.
Two days after he descended, Moshe Rabbenu, 'a"h, again ascended Har Sinai (Mount Sinai), on the 19th of Tammuz, to ask G-d for forgiveness. He remained there for a period of 40 days and 40 nights.
Moshe Rabbenu, 'a"h, ascended Har Sinai (Mount Sinai) for the third time on Rosh Hodesh (the new moon of the month of) Elul. He returned on the 10th of Tashri - Yom Kippur - with the second set of Tablets of Stone, when G-d said "Salahti Kidbarekha" (I have forgiven in accordance with your words).
Since that time, these 40 days from the beginning of Elul till Yom Kippur have become a time for Teshubah (repentance). While Teshubah can be made at all times, this time of year is the most appropriate, for it is set aside for that purpose.
The month of Elul, therefore, which is the last month before the "Days of Awe", Rosh Hashanah and Yom Kippur – is a time when we should dedicate our thoughts to repentance in all things and examine our deeds. From the day after Rosh Hodesh Elul till Yom Kippur, Sephardim rise in the last hours of the night to read Selihoth (penitential prayers). Ashkenazim start Selihoth later. The actual date depends on the year.They are read in these early hours because it is a time of mercy.
Therefore, if one is at a synagogue where they are read in the evening during 'Arbith (the evening prayer), he should sit quietly and not join in. If he wishes to read something else, he may, but he must remember that Sepharadim are very strict not to read the Bible (the Written Law) at night – in accordance with the teachings of Rab Ari, z"I – and he should read from the Oral Law (i.e. Mishnah and Gemara instead.
The Bible (Written Law) is Deen ( judgement), and night is a time of judgement, therefore, according to the Qabbalah, all portions of the 24 Books of the Bible should only be read during the day, which is a time of mercy.
The Selihoth contain many beautiful and often haunting melodies and should be read properly, with understanding and with tears in ones eyes. They should be read with feeling to stir the Attribute of Mercy in The Holy One Blessed Be He, and not like those who shout at the top of their voices oblivious to the meaning of the words of supplication emanating from their mouths.
And about them the holy Rab Hida (may his merit protect us, amen), has written: "He must humble his... heart and must not shout like one who stands in the street; and a fool will not understand what he is saying... "Do they not know thatI its name is 'SELIHOTH' (penitential prayers) and not 'SE'AQOTH' (shouting)?"
The Hazzan (cantor) must be a very worthy individuaL He is the one chosen to lead the entire congregation and must be, therefore, one to whom the Miswoth (precepts) are very dear and one who will assist the congregation in receiving forgiveness from the Al- mighty, and not – Heaven forbid - one who will make their lot all the more difficult. For this reason, it is preferable not to auction who will be the Hazzan but rather give the honor to a praiseworthy individual.
If one were to pray Shahrith (the morning prayers) late, or fall asleep while wearing ones Tephilleen, because one woke early to read Selihoth, it would be better not to read the Selihoth, but to pray correctly. As Rab Hida, 'a"h, says:
"Our Service to G-d consists of preserving the essentials and adding to them - and not of demeaning the essentials to take on additionals."
Ashkenazim read Selihoth for a shorter period of time and have different ones for each day of the week.
The Shofar is blown in Ashkenazi communities during the month of Elul. It is likewise blown, nowadays, in several Sepharadi communities, but not all. The minhagh of the Ben Ish Hai is to not blow at all during the month of Elul. Likewise, the shofar is blown at Midrash BEN ISH HAI, on Rosh Hashanah and Mosi Yom Kippur only.
The 25th of Elul was the first day of the creation of the world. On this day we eat good foods, give more in charity and on the eve of the 25th we kindle five lights. When the eve falls on Friday night, they should obviously be lit prior to the Shabbath (Sabbath) lights. There are special readings prescribed for the "Six Days of Creation", which are explained brought down in the holy work "Leshon Hakhamim" by Hakham Yoseph Hayyim, may his merit protect us, amen.
Happy is he who is able to fast on one or more days during this month. But even those who cannot, should increase their charity and learning of Zohar, Tiqquneen, Mishnah and Tehilleem. Just as we must wish our friends, at the beginning of every letter we write this month, so too we pray for all Israel that we may be inscribed and sealed for a good year.
Taken from the writings of Hakham Ya'aqob Menashe.
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