diff --git a/CHANGELOG.md b/CHANGELOG.md
index 36966fdfd681..fc3c27c14c83 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - _Experimental_: Add `@container-size` utility ([#18901](https://github.com/tailwindlabs/tailwindcss/pull/18901))
 
+### Changed
+
+- Improve canonicalization for `& > :pseudo` and `& :pseudo` arbitrary variants ([#19178](https://github.com/tailwindlabs/tailwindcss/pull/19178))
+
 ### Fixed
 
 - Discard candidates with an empty data type ([#19172](https://github.com/tailwindlabs/tailwindcss/pull/19172))
diff --git a/packages/tailwindcss/src/canonicalize-candidates.test.ts b/packages/tailwindcss/src/canonicalize-candidates.test.ts
index bcf992a886ea..c5599d181c09 100644
--- a/packages/tailwindcss/src/canonicalize-candidates.test.ts
+++ b/packages/tailwindcss/src/canonicalize-candidates.test.ts
@@ -857,6 +857,11 @@ describe.each([['default'], ['with-variant'], ['important'], ['prefix']])('%s',
       ['[&:first-child]:flex', 'first:flex'],
       ['[&:not(:first-child)]:flex', 'not-first:flex'],
 
+      ['[&_:first-child]:flex', '**:first:flex'],
+      ['[&_>_:first-child]:flex', '*:first:flex'],
+      ['[&_:--custom]:flex', '**:[:--custom]:flex'],
+      ['[&_>_:--custom]:flex', '*:[:--custom]:flex'],
+
       // in-* variants
       ['[p_&]:flex', 'in-[p]:flex'],
       ['[.foo_&]:flex', 'in-[.foo]:flex'],
diff --git a/packages/tailwindcss/src/canonicalize-candidates.ts b/packages/tailwindcss/src/canonicalize-candidates.ts
index fd8b862490cf..13c3bc257a91 100644
--- a/packages/tailwindcss/src/canonicalize-candidates.ts
+++ b/packages/tailwindcss/src/canonicalize-candidates.ts
@@ -1610,7 +1610,7 @@ function modernizeArbitraryValuesVariant(
         ast[1].kind === 'combinator' &&
         ast[1].value.trim() === '>' &&
         ast[2].kind === 'selector' &&
-        isAttributeSelector(ast[2])
+        (isAttributeSelector(ast[2]) || ast[2].value[0] === ':')
       ) {
         ast = [ast[2]]
         prefixedVariant = designSystem.parseVariant('*')
@@ -1628,7 +1628,7 @@ function modernizeArbitraryValuesVariant(
         ast[1].kind === 'combinator' &&
         ast[1].value.trim() === '' && // space, but trimmed because there could be multiple spaces
         ast[2].kind === 'selector' &&
-        isAttributeSelector(ast[2])
+        (isAttributeSelector(ast[2]) || ast[2].value[0] === ':')
       ) {
         ast = [ast[2]]
         prefixedVariant = designSystem.parseVariant('**')
@@ -1742,7 +1742,19 @@ function modernizeArbitraryValuesVariant(
           return null
         })(targetNode.value)
 
-        if (newVariant === null) continue
+        if (newVariant === null) {
+          if (prefixedVariant) {
+            replaceObject(variant, {
+              kind: 'arbitrary',
+              selector: target.value,
+              relative: false,
+            } satisfies Variant)
+
+            return [prefixedVariant, variant]
+          }
+
+          continue
+        }
 
         // Add `not-` prefix
         if (compoundNot) newVariant = `not-${newVariant}`