diff --git a/src/util/applyImportantSelector.js b/src/util/applyImportantSelector.js
index ff9ec4f4b343..07302f94d5f6 100644
--- a/src/util/applyImportantSelector.js
+++ b/src/util/applyImportantSelector.js
@@ -5,13 +5,12 @@ export function applyImportantSelector(selector, important) {
   let sel = parser().astSync(selector)
 
   sel.each((sel) => {
-    // Wrap with :is if it's not already wrapped
-    let isWrapped =
-      sel.nodes[0].type === 'pseudo' &&
-      sel.nodes[0].value === ':is' &&
-      sel.nodes.every((node) => node.type !== 'combinator')
+    // For nesting, we only need to wrap a selector with :is() if it has a top-level combinator,
+    // e.g. `.dark .text-white`, to be independent of DOM order. Any other selector, including
+    // combinators inside of pseudos like `:where()`, are ok to nest.
+    let shouldWrap = sel.nodes.some((node) => node.type === 'combinator')
 
-    if (!isWrapped) {
+    if (shouldWrap) {
       sel.nodes = [
         parser.pseudo({
           value: ':is',
diff --git a/tests/util/apply-important-selector.test.js b/tests/util/apply-important-selector.test.js
index f5d3697cf88c..cd971b92c732 100644
--- a/tests/util/apply-important-selector.test.js
+++ b/tests/util/apply-important-selector.test.js
@@ -2,24 +2,23 @@ import { applyImportantSelector } from '../../src/util/applyImportantSelector'
 
 it.each`
   before                                                        | after
-  ${'.foo'}                                                     | ${'#app :is(.foo)'}
+  ${'.foo'}                                                     | ${'#app .foo'}
   ${'.foo .bar'}                                                | ${'#app :is(.foo .bar)'}
-  ${'.foo:hover'}                                               | ${'#app :is(.foo:hover)'}
+  ${'.foo:hover'}                                               | ${'#app .foo:hover'}
   ${'.foo .bar:hover'}                                          | ${'#app :is(.foo .bar:hover)'}
-  ${'.foo::before'}                                             | ${'#app :is(.foo)::before'}
-  ${'.foo::before'}                                             | ${'#app :is(.foo)::before'}
-  ${'.foo::file-selector-button'}                               | ${'#app :is(.foo)::file-selector-button'}
-  ${'.foo::-webkit-progress-bar'}                               | ${'#app :is(.foo)::-webkit-progress-bar'}
-  ${'.foo:hover::before'}                                       | ${'#app :is(.foo:hover)::before'}
+  ${'.foo::before'}                                             | ${'#app .foo::before'}
+  ${'.foo::file-selector-button'}                               | ${'#app .foo::file-selector-button'}
+  ${'.foo::-webkit-progress-bar'}                               | ${'#app .foo::-webkit-progress-bar'}
+  ${'.foo:hover::before'}                                       | ${'#app .foo:hover::before'}
   ${':is(:where(.dark) :is(:where([dir="rtl"]) .foo::before))'} | ${'#app :is(:where(.dark) :is(:where([dir="rtl"]) .foo))::before'}
   ${':is(:where(.dark) .foo) .bar'}                             | ${'#app :is(:is(:where(.dark) .foo) .bar)'}
   ${':is(.foo) :is(.bar)'}                                      | ${'#app :is(:is(.foo) :is(.bar))'}
   ${':is(.foo)::before'}                                        | ${'#app :is(.foo)::before'}
-  ${'.foo:before'}                                              | ${'#app :is(.foo):before'}
-  ${'.foo::some-uknown-pseudo'}                                 | ${'#app :is(.foo)::some-uknown-pseudo'}
-  ${'.foo::some-uknown-pseudo:hover'}                           | ${'#app :is(.foo)::some-uknown-pseudo:hover'}
-  ${'.foo:focus::some-uknown-pseudo:hover'}                     | ${'#app :is(.foo:focus)::some-uknown-pseudo:hover'}
-  ${'.foo:hover::some-uknown-pseudo:focus'}                     | ${'#app :is(.foo:hover)::some-uknown-pseudo:focus'}
+  ${'.foo:before'}                                              | ${'#app .foo:before'}
+  ${'.foo::some-uknown-pseudo'}                                 | ${'#app .foo::some-uknown-pseudo'}
+  ${'.foo::some-uknown-pseudo:hover'}                           | ${'#app .foo::some-uknown-pseudo:hover'}
+  ${'.foo:focus::some-uknown-pseudo:hover'}                     | ${'#app .foo:focus::some-uknown-pseudo:hover'}
+  ${'.foo:hover::some-uknown-pseudo:focus'}                     | ${'#app .foo:hover::some-uknown-pseudo:focus'}
 `('should generate "$after" from "$before"', ({ before, after }) => {
   expect(applyImportantSelector(before, '#app')).toEqual(after)
 })