נָת֤וֹן תִּתֵּן֙ ל֔וֹ וְלֹא־יֵרַ֥ע לְבָבְךָ֖ בְּתִתְּךָ֣ ל֑וֹ כִּ֞י בִּגְלַ֣ל ׀ הַדָּבָ֣ר הַזֶּ֗ה יְבָרֶכְךָ֙ יְהוָ֣ה אֱלֹהֶ֔יךָ בְּכָֽל־מַעֲשֶׂ֔ךָ וּבְכֹ֖ל מִשְׁלַ֥ח יָדֶֽךָ׃
Lo darai sicuramente, e il tuo cuore non sarà rattristato quando gli dai; perché per questo l'Eterno, il tuo DIO, ti benedirà in tutto il tuo lavoro e in tutto ciò a cui metti la mano.
Shaarei Teshuvah
“Give to him readily and have no regrets when you give to him” (Deuteronomy 15:10). We were warned with this to distance our souls from miserliness, but rather to be generous - like the matter that is stated (Proverbs 22:9), “The generous man is blessed.” And it is not enough with the gifts of our hands, but we must rather plant the trait of generosity into our souls. Therefore, it warned and said, “and have no regrets,” after it is stated, “Give to him readily.”
Orchot Tzadikim
He who gives alms to the poor grudgingly loses the merit of the deed, even though he gives much, and it is better that he give only one pruta with a pleasing countenance. And it is well to give before one is asked, and it is well to give secretly, as it is written, "A gift in secret pacifieth anger" (Prov. 21:14). There were people who used to tie the money in a garment and cast it behind them and the poor would come and take, so that he who gave the alms did not know to whom he gave, and he who received the alms did not know from whom he received it, and thus the poor man was not shamed. The general rule in this matter is that as much as possible should be concealed, so that the poor man does not know who is the giver and the giver does not know who is the recipient.
Shenei Luchot HaBerit
The commandment to provide a Jewish servant [generally someone who has worked for the master for six years. Ed.] who leaves one's employment with a stake, as per 15,14 falls under the heading of both צדקה and גמילות חסדים. The remission of outstanding debts at the end of the Shemittah year as well as the generosity displayed towards a servant leaving one's employment allude to the reward G–d will pay to those who serve Him faithfully. The whole subject of the שמטה, seventh year, legislation alludes to a world which is totally based on the concept of the Sabbath, the period when the reward for מצות performed in this world will be collected. G–d will יגוש, "dun" us for what we owe Him. He will instead pay us a generous reward because we have fulfilled our duties towards others as outlined in the legislation in this chapter.