The commandment1 to give tzedakah (charity) is included in the Torah portion of Re’eh, where the verse states:2 “Should there be amongst you a pauper… do not harden your heart or shut your hand against your needy brother. Open your hand generously.”

The section of Re’eh is invariably read on the Shabbos on which we bless the new month of Elul, or on Rosh Chodesh Elul itself. Since all Torah portions are related to the timeframe in which they are read,3 it follows that it is especially appropriate to give tzedakah during the month of Elul.

This may be derived from the following statement by the Rambam :4 “Although sounding the shofar on Rosh HaShanah is a decree for which the verse does not state a reason, nevertheless, it also hints at something specific, i.e., ‘Awake, you who sleep… and better your ways….’

“Each and every person is to see himself… as half righteous…. By performing one mitzvah, he tips the scales for himself and for the entire world on the side of merit, bringing deliverance and salvation for himself and for all others.

“For this reason, all Jews customarily increase their giving of tzedakah and performance of good deeds and mitzvos … from Rosh HaShanah through Yom Kippur, more so than during the rest of the year…. They also rise at night during these ten days… and offer supplicatory prayers until daylight.”

Since the Rambam specifies the custom of “increasing the amount given for tzedakah ,” and moreover gives it precedence over all other things that are done during these ten days, it follows that although all aspects of Torah and mitzvos are to be strengthened during this period, one should first and foremost increase one’s giving of tzedakah.

And so too with regard to the month of Elul, which is similar to the Ten Days of Penitence in many ways:

a) the Month of Repentance5 is similar to the Ten Days of Penitence;

b) just as these ten days are days of preparation for the decisive day of Yom Kippur , so too the month of Elul serves as days of preparation for Rosh HaShanah.

c) Moreover, the entire period from the beginning of the month of Elul until after Yom Kippur constitutes one long chain of repentance.6

It is thus readily understandable that, just as one increases one’s giving of tzedakah during the Ten Days of Penitence, so too should one increase one’s distribution of tzedakah during the entire month of Elul.

What quality does tzedakah possess that causes it to be singled out as the primary mitzvah to be enhanced during the month of Elul?

The month of Elul is a month of “mercy and forgiveness,” so much so that “some people have the custom of reciting supplicatory prayers for forgiveness from Rosh Chodesh Elul and onward.”7 On the other hand, although the month itself is one during which G‑d’s mercy radiates, the recitation of supplicatory prayers for forgiveness helps ensure that the supplicant will be judged favorably by G‑d — “Increasing one’s supplications for mercy is considered a merit for the individual.”8

These two themes seem to be contradictory: Beseeching G‑d’s mercy presupposes that a person is lacking merit and thus must ask G‑d to judge him favorably nonetheless. Yet, when we say that the beseeching of G‑d’s mercy acts as a merit for the individual, we are implying that mercy is not needed, since his prayers provide him with merit.

The answer to this seeming contradiction, which also arises when considering the need to increase the giving of tzedakah during the month of Elul, is as follows: One merits to be judged favorably during the month of Elul precisely by coming to understand that no matter how good one may be, there is always a need for G‑d’s mercy,9 so that He acts towards one gratuitously and with tzedakah.

This Divine attribute is roused when a person acts in a similar manner toward his fellow.

Based on Likkutei Sichos, Re’eh-Elul 5748