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1. Opening Scripture

But he was pierced for our transgressions; he was crushed for our iniquities…
 Isaiah 53:5–6 

This passage highlights two related but distinct terms: transgression and iniquity.

Other Scriptures (such as Exodus 34:7 and Psalm 32:5) list iniquity, transgression, and sin together, showing that while they overlap, they carry distinct meanings.

2. Definitions & Distinctions

Sin (ḥaṭṭāʾt / hamartia)

  • Meaning: “To miss the mark” (Romans 3:23).
  • Broadest term for falling short of God’s holiness.

Transgression (peshaʿ)

  • Meaning: “To rebel or cross the line” (1 John 3:4).
  • Willful disobedience against God’s commands.

Iniquity (ʿāwōn / anomia)

  • Meaning: “Crookedness, perversion, inner corruption.”
  • Not just acts but the bent of the heart (Psalm 51:5, Isaiah 59:2).

👉 Iniquity is the root condition, sin is the fruit, and transgression is the rebellion of choosing to act against God.

3. Cross-References

  • Psalm 51:5 — David acknowledges being “brought forth in iniquity.”
  • Psalm 66:18 — “If I regard iniquity in my heart, the Lord will not hear me.”
  • Matthew 7:23 — Jesus: “Depart from me, you workers of iniquity.”
  • James 1:13–15 — Desire → Temptation → Sin → Death.
  • Galatians 5:16–17 — Walking in the Spirit keeps us from fulfilling sinful desires.
  • Romans 6:12–14 — Do not let sin reign in your mortal body.
  • Exodus 34:7 — God forgives iniquity, transgression, and sin.
  • Psalm 32:5 — David distinguishes between sin, iniquity, and transgression in his confession.

4. Commentary

  • Iniquity and Sin: Iniquity is the inward distortion of God’s design. Sin is the outward manifestation.
  • Iniquity and Transgression: Iniquity is the bent of heart; transgression is willful rebellion.
  • Iniquity and Temptation: Temptation entices from outside, but iniquity resonates with it, making it appealing.
  • God’s Solution: Christ bore both our transgressions (acts) and iniquities (heart corruption) on the cross (Isaiah 53:5).

5. Insightful Questions

  1. Why is it important to distinguish between iniquity, transgression, and sin?
  2. How does recognizing iniquity in the heart help us understand our struggles with sin?
  3. In what ways can unchecked iniquity block our fellowship with God (Psalm 66:18)?
  4. How do Galatians 5:16–17 and Romans 6:12–14 show us the Spirit’s role in overcoming iniquity?
  5. .What does it mean that Christ was “crushed for our iniquities” (Isaiah 53:5)?

6. Life Applications

  • Pray like David: Ask God for cleansing not just from sins but from iniquities (Psalm 51:10).
  • Guard the Heart: Root out hidden crookedness before it bears fruit (Proverbs 4:23).
  • Rely on the Spirit: Daily yield to the Spirit to weaken sinful desires (Galatians 5:16).
  • Confess Both Root and Fruit: When repenting, confess not just sinful acts but the crookedness beneath them.
  • Rest in Christ’s Work: Trust that Jesus’ sacrifice addresses both the inward bent and outward sins.

7. Closing Thought

Iniquity is the hidden crookedness, transgression is the open rebellion, temptation is the external bait, and sin is when we take the hook. Christ redeems us from all of these.