Do not give more than a fifth (takanas Usha)
The Sages capped charitable giving at twenty percent of one's means so the giver does not become impoverished. The app warns when cumulative giving exceeds 20% of income, while noting the recognized exceptions (great wealth, deathbed bequests).
Positions by community
Ashkenazi
Kesubos 50a: 'In Usha they instituted: one who dispenses should not dispense more than a fifth, lest he become dependent on others.' Codified by the Rema (YD 249:1), who adds the cap applies during one's lifetime but not to end-of-life bequests; exceptions are discussed for the very wealthy.
Sephardi
Same Gemara and codification.
Chabad
Same Gemara and codification; Chassidic sources discuss additional latitude in certain circumstances — consult a rav.
Sources
- https://www.sefaria.org/Ketubot.50a — Kesubos 50a
- https://www.sefaria.org/Shulchan_Arukh,_Yoreh_De'ah.249.1 — Yoreh De'ah 249:1 (gloss)
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MyMaaser presents sourced halachic positions and is not a substitute for your rav. Consult your rav (CYLOR).