What does Psalm 23:5 mean?

This verse may describe a gracious host as he provides a banquet for an honored guest, or it may continue the metaphor of the shepherd-sheep relationship. If it refers to a host preparing a banquet, David views himself as the Lord's honored guest with David's enemies present as captive onlookers.

If it refers to a shepherd-sheep relationship, David compares the Lord's generosity to that of a shepherd who generously prepares a feast for his sheep, spreading the food on a table or trough. As the sheep slept, they were protected by a circular stone wall and the shepherd who slept across the opening. Jesus identified Himself as the door to the sheepfold (John 10:7–9).

A gracious host would anoint his guest by applying a soothing oil to the guest's head. A shepherd would use oil to treat his sheep's wounds. David may have been thinking about the Lord as his host or shepherd when he wrote, "you anoint my head with oil" (Psalm 23:5). The cup David depicts as overflowing may refer to the brimming cup the host provided or to the large cup a shepherd used to give water to thirsty sheep. Either interpretation leads to the conclusion that the Lord provides for us more generously than the heart can desire.