diff --git a/CHANGELOG.md b/CHANGELOG.md
index d6ef24b4883a..0d1528b096e6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Fixed use of `raw` content in the CLI ([#9773](https://github.com/tailwindlabs/tailwindcss/pull/9773))
 - Pick up changes from files that are both context and content deps ([#9787](https://github.com/tailwindlabs/tailwindcss/pull/9787))
+- Sort pseudo-elements ONLY after classes when using variants and `@apply` ([#9765](https://github.com/tailwindlabs/tailwindcss/pull/9765))
 
 ## [3.2.2] - 2022-11-04
 
diff --git a/src/lib/expandApplyAtRules.js b/src/lib/expandApplyAtRules.js
index e1453af0152a..8ca50fb99ae9 100644
--- a/src/lib/expandApplyAtRules.js
+++ b/src/lib/expandApplyAtRules.js
@@ -370,9 +370,9 @@ function processApply(root, context, localCache) {
                 return -1
               } else if (a.type === 'class' && b.type === 'tag') {
                 return 1
-              } else if (a.type === 'class' && b.type === 'pseudo') {
+              } else if (a.type === 'class' && b.type === 'pseudo' && b.value.startsWith('::')) {
                 return -1
-              } else if (a.type === 'pseudo' && b.type === 'class') {
+              } else if (a.type === 'pseudo' && a.value.startsWith('::') && b.type === 'class') {
                 return 1
               }
 
diff --git a/src/util/formatVariantSelector.js b/src/util/formatVariantSelector.js
index ffcc5f037eed..ae6aa69a0a29 100644
--- a/src/util/formatVariantSelector.js
+++ b/src/util/formatVariantSelector.js
@@ -69,9 +69,9 @@ function resortSelector(sel) {
       return -1
     } else if (a.type === 'class' && b.type === 'tag') {
       return 1
-    } else if (a.type === 'class' && b.type === 'pseudo' && b.value !== ':merge') {
+    } else if (a.type === 'class' && b.type === 'pseudo' && b.value.startsWith('::')) {
       return -1
-    } else if (a.type === 'pseudo' && a.value !== ':merge' && b.type === 'class') {
+    } else if (a.type === 'pseudo' && a.value.startsWith('::') && b.type === 'class') {
       return 1
     }
 
diff --git a/tests/apply.test.js b/tests/apply.test.js
index 5eb8ecb38151..6f7214d990ab 100644
--- a/tests/apply.test.js
+++ b/tests/apply.test.js
@@ -1601,6 +1601,9 @@ it('can apply joined classes when using elements', async () => {
     header:nth-of-type(odd) {
       @apply foo;
     }
+    header::after {
+      @apply foo;
+    }
     main {
       @apply foo bar;
     }
@@ -1618,7 +1621,13 @@ it('can apply joined classes when using elements', async () => {
     .bar.foo {
       color: green;
     }
+    header:nth-of-type(odd).bar {
+      color: red;
+    }
     header.bar:nth-of-type(odd) {
+      color: green;
+    }
+    header.bar::after {
       color: red;
       color: green;
     }
@@ -1721,21 +1730,15 @@ it('should maintain the correct selector when applying other utilities', () => {
 
   return run(input, config).then((result) => {
     expect(result.css).toMatchFormattedCss(css`
-      .foo.bar:hover .baz {
+      .foo:hover.bar .baz {
         --tw-bg-opacity: 1;
         background-color: rgb(0 0 0 / var(--tw-bg-opacity));
-      }
-
-      .foo:hover.bar .baz {
         color: red;
       }
 
-      .foo.bar:hover > .baz {
+      .foo:hover.bar > .baz {
         --tw-bg-opacity: 1;
         background-color: rgb(0 0 0 / var(--tw-bg-opacity));
-      }
-
-      .foo:hover.bar > .baz {
         color: red;
       }
     `)
diff --git a/tests/variants.test.js b/tests/variants.test.js
index e05c826fdfc2..6de7c3dd0caf 100644
--- a/tests/variants.test.js
+++ b/tests/variants.test.js
@@ -861,12 +861,12 @@ test('multi-class utilities handle selector-mutating variants correctly', () =>
     content: [
       {
         raw: html`<div
-          class="hover:foo hover:bar hover:baz group-hover:foo group-hover:bar group-hover:baz peer-checked:foo peer-checked:bar peer-checked:baz"
+          class="after:foo after:bar after:baz hover:foo hover:bar hover:baz group-hover:foo group-hover:bar group-hover:baz peer-checked:foo peer-checked:bar peer-checked:baz"
         ></div>`,
       },
       {
         raw: html`<div
-          class="hover:foo1 hover:bar1 hover:baz1 group-hover:foo1 group-hover:bar1 group-hover:baz1 peer-checked:foo1 peer-checked:bar1 peer-checked:baz1"
+          class="after:foo1 after:bar1 after:baz1 hover:foo1 hover:bar1 hover:baz1 group-hover:foo1 group-hover:bar1 group-hover:baz1 peer-checked:foo1 peer-checked:bar1 peer-checked:baz1"
         ></div>`,
       },
     ],
@@ -885,15 +885,45 @@ test('multi-class utilities handle selector-mutating variants correctly', () =>
     }
   `
 
+  // The second set of ::after cases (w/ descendant selectors)
+  // are clearly "wrong" BUT you can't have a descendant of a
+  // pseudo - element so the utilities `after:foo1` and
+  // `after:bar1` are non-sensical so this is still
+  // perfectly fine behavior
+
   return run(input, config).then((result) => {
     expect(result.css).toMatchFormattedCss(css`
-      .hover\:foo.bar.baz:hover {
+      .after\:foo.bar.baz::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .after\:bar.foo.baz::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .after\:baz.foo.bar::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .after\:foo1 .bar1 .baz1::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .foo1 .after\:bar1 .baz1::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .foo1 .bar1 .after\:baz1::after {
+        content: var(--tw-content);
+        color: red;
+      }
+      .hover\:foo:hover.bar.baz {
         color: red;
       }
-      .hover\:bar.foo.baz:hover {
+      .hover\:bar:hover.foo.baz {
         color: red;
       }
-      .hover\:baz.foo.bar:hover {
+      .hover\:baz:hover.foo.bar {
         color: red;
       }
       .hover\:foo1:hover .bar1 .baz1 {