05/13/2026
When Your Cup Really Overflows
By: Paul Tautges
May 13, 2026
Doubt, Goodness, Psalm 23
Recently, I stood with my son at the Franklin Delano Roosevelt Memorial in Washington, D.C. One scene stopped me—the bronze figures of weary men waiting in a bread line. Their shoulders slumped, their faces marked by fear and uncertainty, their hands empty. It’s a quiet but powerful reminder of a time when people desperately hoped for daily bread instead of assuming they would have it.
As I stood there, I found myself thinking back almost twenty years to visiting that same memorial with my dad. He didn’t just observe that bread line—he felt it. Having lived through the Depression and served in the infantry during World War II, he understood what it meant to lack daily provisions. That bread line is a picture of longing and scarcity.
But Psalm 23:5 gives us a strikingly different image: “You prepare a table before me… my cup overflows.” Our Shepherd is not merely a provider of bare necessities—He is an exceedingly generous host. He does not call us to stand in line, uncertain and empty-handed, but to sit at His table, where there is abundance, welcome, and more than enough.
In Psalm 23, how do we get from “the valley of the shadow of death” in verse 4 to “You prepare a table before me… you anoint my head with oil; my cup overflows”? The imagery shifts from Shepherd to Host, but the person is the same. The one who walked through the valley of darkness before you, and for you, is now the one who delights to bless you with abundant hospitality.
Psalm 23:5 paints His hospitality in three ways.
You Are Secure at His Table
To “prepare a table” is to prepare a meal—to show gracious hospitality to one’s guests. In Psalm 78, Asaph reviews Israel’s distrust of God’s provision:
“They tested God in their heart
by demanding the food they craved.
They spoke against God, saying,
‘Can God spread a table in the wilderness?’”
David’s answer in Psalm 23 is: yes, He can. And not only can God prepare a table; He does so “in the presence of my enemies.”
David may be thinking back to the time he fled from Absalom, when the Lord moved ordinary people to meet him in the wilderness with food and supplies because “the people are hungry and weary and thirsty in the wilderness” (2 Sam. 17:27-29). God literally spread a table for David in the presence of his enemies.
What about you? Perhaps you feel surrounded—by medical tests, strained relationships, financial pressures, or spiritual attacks. This verse says: even there, the Shepherd can spread a table for you. Your enemies may still be present, but they are no longer in charge. They watch; they cannot touch the table.
People often assume, “If God really loved me, He would remove all my problems.” Psalm 23:5 says something different: the Shepherd may not remove every enemy yet, but He feeds His people in full view of what threatens them. There is actual security at His table because He has already secured victory.
You Are Lavished with Grace
“You anoint my head with oil…” It carries the idea of abundance—richness, fullness. You could translate it, “You make my head rich with oil,” or in our language, “You slather my head with oil.”
Yesterday morning, we did some “slathering” in our kitchen. My daughter made a pan of our family’s favorite cinnamon rolls, and I mixed up a triple batch of glaze. When the rolls cooled, she slathered them with frosting; they were dripping with sugary richness. That’s the picture here—not a thin coating of grace, but a generous slathering until it runs over the edges.
In the New Testament, the lavishness of God’s grace shines most brightly in the gift of His Son. Ephesians 1 tells us that in Christ we have redemption through His blood, the forgiveness of our trespasses, “according to the riches of His grace, which He lavished upon us.” This is the grace Psalm 23:5 points us toward—grace not measured out sparingly but poured out richly in Christ.
For counselees who live under a constant sense of being merely tolerated by God, this image is crucial: the Shepherd does not dab a little mercy on your forehead; He slathers you with it.
Your Cup Overflows
In David’s world, an overflowing cup signified that the host still wanted to engage with you. Instead of filling the cup and stopping, the host kept pouring. The overflowing cup said, “You are welcome here. I have more for you.”
In Pride and Prejudice, there’s a moment when Elizabeth tries to explain her love for Mr. Darcy to her father. He cannot understand; he still sees Darcy as proud and distant. Elizabeth pleads, “If you only knew what he is!” You’re judging him based on what you’ve seen, but you don’t know his heart.
Isn’t that, in a deeper way, how many Christians think about God?
We believe in Him. We worship Him. But when it comes to His heart toward us, we often live as if He were reluctant, stingy with His grace. We fear He will give us only the bare minimum.
But Scripture says something entirely different. Psalm 23:5 declares abundance—lavish, unembarrassed generosity. “If you only knew what He is!”
If you only knew how generous your Shepherd is…
If you only knew how He delights to answer your prayers…
If you only knew the extravagance of His grace…
The problem is not that God is withholding His kindness. The problem is that we often misunderstand His heart.
Romans 8:32 forces the issue: “He who did not spare his own Son but gave him up for us all, how will he not also with him graciously give us all things?” The cross is the greatest argument against the suspicion that God is stingy. If He has already given His beloved Son, we can trust Him with every lesser need. The more we grow in knowing the depth of God’s love for us in Christ, the more we will trust His heart, ask boldly, and rest in His overflowing goodness.
We start as sheep in the valley and end as guests at the table because the Shepherd has already walked through the valley of the shadow of death before you and for you. He did all of this to bring you safely home and seat you at His table.
