Biblically Prescribed Generosity

Generosity is not always Biblically optional.  There are a great many forms it can take where it is not sinful to forgo a given expression of generosity, but there are several particular ways that freely giving to others is required, or particular scenarios where denying people access to one's material resources by neglect or force is sin.  Note below how all people are morally free to take from the standing crops of a person's field, yet not more than they can carry in their hands and eat; this is not theft, which is always evil (Exodus 20:15, 22:1-4, Numbers 5:5-7), and thus being generous in this manner, among others to soon be elaborated upon, is obligatory.  This of course applies to the poor and those who are not destitute, though it is of special benefit to the financially insecure.

Leviticus 19:9-10--"'"When you reap the harvest of your land, do not reap to the very edges of your field or gather the gleanings of your harvest.  Do not go over your vineyard a second time or pick up the grapes that have fallen.  Leave them for the poor and the foreigner.  I am the Lord your God."'"

Deuteronomy 23:24-25--"If you enter your neighbor's vineyard, you may eat all the grapes you want, but do not put any in your basket.  If you enter your neighbor's grainfield, you may pick kernels with your hand, but you must not put a sickle to their standing grain."

Deuteronomy 24:19-21--"When you are harvesting in your field and you overlook a sheaf, do not go back to get it.  Leave it for the foreigner, the fatherless and the widow, so that the Lord your God may bless you in all the work of your hands.  When you beat the olives from your trees, do not go over the branches a second time.  Leave what remains for the foreigner, the fatherless and the widow.  When you harvest the grapes in your vineyard, do not go over the vines again.  Leave what remains for the foreigner, the fatherless and the widow."

Beyond just leaving agricultural excess in place for the societally disadvantaged without discrimination based upon their gender or nationality/ancestry, regarding the general approach to the poor, Deuteronomy demands that people not withhold assisting them even when the mandatory year for the cancellation of debts is near (Deuteronomy 15:1-3; how unlike American norms this is!).  Generosity, when someone can genuinely afford it, is required in the sense that people are not to be "tightfisted" with their wealth when faced with those less prosperous than them.  While, for instance, giving to a particular random homeless person is not obligatory, neglecting the general poor beyond refusing to leave the specified portions of one's crops for them is directly condemned:

Deuteronomy 15:7-10--"If anyone is poor among your fellow Israelites in any of the towns of the land the Lord your God is giving you, do not be hardhearted or tightfisted towards them.  Rather, be openhanded and freely lend them whatever they need.  Be careful not to harbor this wicked thought: 'The seventh year, the year for cancelling debts, is near,' so that you do not show ill will towards the needy among your fellow Israelites and give them nothing.  They may then appeal to the Lord against you, and you will be found guilty of sin.  Give generously to them and do so without a grudging heart; then because of this the Lord your God will bless you in all your work and in everything you put your hand to."

Verses 12-17 right after this are relevant to generosity as well.  The way that the use of temporary servitude is listed immediately after these details about how to treat the poor in one's community, without explicitly saying this, points to how this kind of slavery, in which the man or woman is to be treated well (Exodus 20:8-11, 23:12, and so on) to the point of potentially wanting to remain a slave for life (Exodus 21:2-6, Deuteronomy 15:16-17) or else they go free with no opposition (Exodus 21:26-27, Deuteronomy 23:15-16), is an ideal way to escape poverty.  Not only would the poor person have the option of selling their labor to an individual household while possessing every rigid human right affirmed in the Torah, as opposed to working for a profit-driven and exploitative corporation or resorting to theft or other sins to survive, but he or she is also to be freed after six years of servitude and given abundant material resources on their way out.  Even pragmatically as opposed to morally, this is obviously a superior way over the modern American employment system to actually curb poverty without dehumanizing workers:

Deuteronomy 15:12-14--"If any of your people--Hebrew men or women--sell themselves to you and serve you six years, in the seventh year you must let them go free.  And when you release them, do not send them away empty-handed.  Supply them liberally from your flock, your threshing floor and your winepress.  Give to them as the Lord your God has blessed you."

It is not just generosity to freed servants that is commanded by God.  Giving to the Levite, foreigner, fatherless, and widow from a person's supply of food yielded by the Promised Land is explicitly codified.  While giving to the Levites in the third year of residence in the Promised Land is no longer possible and thus cannot be morally obligatory, the remaining prescriptions already addressed here are not, since they are accessible today and thus required.  Yes, the following passage deals with something which is not universal in its binding nature (see Deuteronomy 26:1-11 for context) as with something like an agricultural community intentionally leaving the aforementioned sorts of food for those most in need, but it still expresses the sort of generosity that is otherwise continually obligatory since it is tied to God's unchanging moral nature (Deuteronomy 4:5-8, Malachi 3:6):

Deuteronomy 26:12-13--"When you have finished setting aside a tenth of all your produce in the third year, the year of the tithe, you shall give it to the Levite, the foreigner, the fatherless and the widow, so that they may eat in your towns and be satisfied.  Then say to the Lord your God: 'I have removed from my house the sacred portion and have given it to the Levite, the foreigner, the fatherless and the widow, according to all you commanded.'"

Again, not every kind of generosity is merely optional.  In the right circumstances, it is an absolute moral necessity on the Christian worldview to give or to not be unwilling to share--the most obvious categories mentioned in the verses I have included here being those of substances needed to live, such as food.  Sharing one's bread with the hungry, which is in no way limited by the teachings of the Bible or the logical necessity of the concept to literal bread, is listed among the miscellaneous just deeds of a righteous person in the book of Ezekiel (18:5, 7, 16).  To do this, which is a matter of justice according to the Torah and Ezekiel, one must be generous.  It is impossible to hold onto one's resources with no intention of benefitting others in any situation and obey certain commands of Yahweh.