God asks the lender to picture the poor man at night. If the garment he gave as security is kept, he has nothing to sleep in. Gill explains that the man "must lie naked without any covering, which to deprive him of would be cruel." Keil & Delitzsch paraphrase the question: "in what shall he wrap himself to sleep?"

The question turns a rule about loans into a matter of the heart. It makes the lender see the borrower as a person with a night to get through. Gill also mentions that the words can be read without a question mark, as a statement of what the poor man sleeps in; either way, the point is the same.

The question needs no answer: the garment "is his covering only, it is his raiment for his skin" (Exodus 22:27), so without it he has nothing. The command has already given the answer: "thou shalt deliver it unto him by that the sun goeth down" (Exodus 22:26). God then adds what He will do: "it shall come to pass, when he crieth unto me, that I will hear; for I am gracious" (Exodus 22:27).

This law sits in a passage that guards the weakest: the stranger, the widow, the fatherless, and the poor (Exodus 22:21-27). Twice God says that when they cry to Him, He will hear (Exodus 22:23, 27). Israel knew this from experience: in Egypt "their cry came up unto God" (Exodus 2:23), and God said, "I ... have heard their cry" (Exodus 3:7).

The reason God gives is His own character: "for I am gracious" (Exodus 22:27). He later proclaims Himself "The LORD, The LORD God, merciful and gracious" (Exodus 34:6), using the same Hebrew word. Keil & Delitzsch say the precepts of Exodus 22:21-27 were aimed, at their deepest root, against "the sins of selfishness and covetousness." The law protects a poor man's garment because God Himself cares how that man sleeps.