During our Rosh HaShanah prayers we make no mention of the fact that Rosh HaShanah is also Rosh Chodesh, the beginning of the new month of Tishrei. The Alter Rebbe states that one of the reasons for this is, “in order to confound Satan, so that he will not know that this day is Rosh Chodesh Tishrei (and thus will not come to ‘accuse’ us on this day of judgment.)”1

This concept of “confounding Satan” is also offered as the reason for the custom of not blessing the new month of Tishrei on the Shabbos that precedes it, as we do during all other months on the Shabbos that precedes the new month.2

Satan is an angel and as such appears in the heavenly court, and the like.3 So how can he be “confounded” and “fooled” and not know when Rosh HaShanah will occur? Moreover, the day of Rosh HaShanah is very well publicized; it is printed in calendars, etc. How can Satan possibly not know the day on which it falls?

“Confounding Satan” is also offered as a reason for sounding the shofar during the month of Elul — Satan is thereby “confounded” and “fails to ascertain when it is Rosh HaShanah.”4 Here, too, the identical question arises: How can Satan be “confounded” into not knowing which day is Rosh HaShanah?

The general theme of confounding Satan (in association with Rosh HaShanah) is found in the Gemara5 with regard to the general element of sounding the shofar on Rosh HaShanah: Rabbi Yitzchak says, “Why do we sound the shofarteki’os and teru’os — while seated and once again while standing? In order to confound Satan.”

Rashi explains the concept of “confounding Satan” as follows: “So that he will not accuse; for when he hears how the Jewish people love the mitzvos, his words of accusation are stifled.”

In other words, since the Jewish people are not content to merely sound the shofar once, but do so over and over again — while seated and while standing — they demonstrate their love for the commandments. This causes the words of Satan to be suppressed.

The same explanation is germane regarding confounding Satan by sounding the shofar throughout the month of Elul:

The shofar is sounded during Elul to “exhort the Jewish people to repent, as the verse says,6 ‘Should a shofar be sounded in a city, will the populace not tremble?’ ”7

Thus, the very fact that Jews sound the shofar and are roused to repentance causes Satan to be confounded, as he takes it as a sure sign that during the month of Elul, the Jewish people were already victorious in their judgment. As a result, he feels that there is no point — he will accomplish absolutely nothing — by accusing and denouncing them on Rosh HaShanah.

In light of the above, we will also understand the meaning of the statement that by confounding Satan through sounding the shofar during Elul, “he fails to ascertain when is Rosh HaShanah.”

The meaning of “failing to ascertain when is Rosh HaShanah” is not to be taken to mean that Satan isn’t aware of the actual day that is declared in the calendar to be Rosh HaShanah.

Rather, it means that Satan won’t know when the specific aspect of the period of judgment of Rosh HaShanah comes about — the point of time when he presents his accusations. This is stated explicitly in the Maharil:8 “He does not know when is the time of judgment; when he isto come and accuse.”

When a Jew repents properly prior to the onset of Rosh HaShanah, then he is already assured that he will be written and sealed in the Book of the Righteous. In other words, by repenting prior to Rosh HaShanah, his judgment for the good was already assured during the month of Elul.

This is especially so since it is indicated in many places that through repentance and prayer it is possible during all the days of the year — not necessarily on Rosh HaShanah — to reach a full and conclusive verdict for absolute good.

An example is King Chezkiyahu9 who, through his prayer and repentance, extended his life by an additional fifteen years.10 Upon closer examination of this episodeas related in Tanach, we realize that King Chezkiyahu did not necessarily effect the lengthening of his life during an especially propitious time such as Rosh HaShanah and the like.11

This is why Satan is confounded and disconcerted by the sounding of the shofar during the month of Elul. Satan thinks that through their arousal to repentance during the month of Elul the Jewish people were already victorious in their judgment for the coming year; and therefore, his accusations will accomplish absolutely nothing.

As a result, even when Satan does present his accusations on Rosh HaShanah, he does so in an indecisive, irresolute and hesitant manner.

Consequently, all of Israel merits to be written and inscribed for a good and sweet year, both materially and spiritually.

Based on Likkutei Sichos, Vol. XXIV, pp. 222-224.