diff --git a/CHANGELOG.md b/CHANGELOG.md
index d19e60de1a94..ff8484795fd8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Changed
 
 - Drop warning from browser build ([#18731](https://github.com/tailwindlabs/tailwindcss/issues/18731))
+- Drop exact duplicate declarations when emitting CSS ([#18809](https://github.com/tailwindlabs/tailwindcss/issues/18809))
 
 ### Fixed
 
diff --git a/packages/tailwindcss/src/ast.test.ts b/packages/tailwindcss/src/ast.test.ts
index 9f879d64b10a..865121c694d4 100644
--- a/packages/tailwindcss/src/ast.test.ts
+++ b/packages/tailwindcss/src/ast.test.ts
@@ -202,6 +202,93 @@ it('should not emit empty rules once optimized', () => {
   `)
 })
 
+it('should not emit exact duplicate declarations in the same rule', () => {
+  let ast = CSS.parse(css`
+    .foo {
+      color: red;
+      .bar {
+        color: green;
+        color: blue;
+        color: green;
+      }
+      color: red;
+    }
+    .foo {
+      color: red;
+      & {
+        color: green;
+        & {
+          color: red;
+          color: green;
+          color: blue;
+        }
+        color: red;
+      }
+      background: blue;
+      .bar {
+        color: green;
+        color: blue;
+        color: green;
+      }
+      caret-color: orange;
+    }
+  `)
+
+  expect(toCss(ast)).toMatchInlineSnapshot(`
+    ".foo {
+      color: red;
+      .bar {
+        color: green;
+        color: blue;
+        color: green;
+      }
+      color: red;
+    }
+    .foo {
+      color: red;
+      & {
+        color: green;
+        & {
+          color: red;
+          color: green;
+          color: blue;
+        }
+        color: red;
+      }
+      background: blue;
+      .bar {
+        color: green;
+        color: blue;
+        color: green;
+      }
+      caret-color: orange;
+    }
+    "
+  `)
+
+  expect(toCss(optimizeAst(ast, defaultDesignSystem))).toMatchInlineSnapshot(`
+    ".foo {
+      .bar {
+        color: blue;
+        color: green;
+      }
+      color: red;
+    }
+    .foo {
+      color: green;
+      color: blue;
+      color: red;
+      background: blue;
+      .bar {
+        color: blue;
+        color: green;
+      }
+      caret-color: orange;
+    }
+    "
+  `)
+})
+
 it('should only visit children once when calling `replaceWith` with single element array', () => {
   let visited = new Set()
 
diff --git a/packages/tailwindcss/src/ast.ts b/packages/tailwindcss/src/ast.ts
index e4b5d5a9ab52..a473b9193e7f 100644
--- a/packages/tailwindcss/src/ast.ts
+++ b/packages/tailwindcss/src/ast.ts
@@ -351,27 +351,45 @@ export function optimizeAst(
 
     // Rule
     else if (node.kind === 'rule') {
-      // Rules with `&` as the selector should be flattened
-      if (node.selector === '&') {
-        for (let child of node.nodes) {
-          let nodes: AstNode[] = []
-          transform(child, nodes, context, depth + 1)
-          if (nodes.length > 0) {
-            parent.push(...nodes)
-          }
-        }
+      let nodes: AstNode[] = []
+
+      for (let child of node.nodes) {
+        transform(child, nodes, context, depth + 1)
       }
 
-      //
-      else {
-        let copy = { ...node, nodes: [] }
-        for (let child of node.nodes) {
-          transform(child, copy.nodes, context, depth + 1)
-        }
-        if (copy.nodes.length > 0) {
-          parent.push(copy)
+      // Keep the last decl when there are exact duplicates. Keeping the *first* one might
+      // not be correct when given nested rules where a rule sits between declarations.
+      let seen: Record<string, AstNode[]> = {}
+      let toRemove = new Set<AstNode>()
+
+      // Keep track of all nodes that produce a given declaration
+      for (let child of nodes) {
+        if (child.kind !== 'declaration') continue
+
+        let key = `${child.property}:${child.value}:${child.important}`
+        seen[key] ??= []
+        seen[key].push(child)
+      }
+
+      // And remove all but the last of each
+      for (let key in seen) {
+        for (let i = 0; i < seen[key].length - 1; ++i) {
+          toRemove.add(seen[key][i])
         }
       }
+
+      if (toRemove.size > 0) {
+        nodes = nodes.filter((node) => !toRemove.has(node))
+      }
+
+      if (nodes.length === 0) return
+
+      // Rules with `&` as the selector should be flattened
+      if (node.selector === '&') {
+        parent.push(...nodes)
+      } else {
+        parent.push({ ...node, nodes })
+      }
     }
 
     // AtRule `@property`
diff --git a/packages/tailwindcss/src/index.test.ts b/packages/tailwindcss/src/index.test.ts
index a19fcf96d979..cbdb88186dc9 100644
--- a/packages/tailwindcss/src/index.test.ts
+++ b/packages/tailwindcss/src/index.test.ts
@@ -527,7 +527,6 @@ describe('@apply', () => {
       .foo, .bar {
         --tw-content: "b";
         content: var(--tw-content);
-        content: var(--tw-content);
       }
 
       @property --tw-content {