diff --git a/packages/vite/src/node/plugins/css.ts b/packages/vite/src/node/plugins/css.ts
index 6830215563f5fa..c3ecac653ecea2 100644
--- a/packages/vite/src/node/plugins/css.ts
+++ b/packages/vite/src/node/plugins/css.ts
@@ -2104,9 +2104,15 @@ const UrlRewritePostcssPlugin: PostCSS.PluginCreator<{
 
   return {
     postcssPlugin: 'vite-url-rewrite',
-    OnceExit(root) {
+    OnceExit(_root, { result }) {
       const promises: Promise<void>[] = []
-      root.walkDecls((declaration) => {
+      // walk `result.root` rather than the `root` argument: a plugin running
+      // earlier (e.g. postcss-lightningcss, @tailwindcss/vite) may hand back a
+      // freshly parsed tree by reassigning `result.root`, and PostCSS keeps
+      // passing the pre-reassignment root to the OnceExit hooks that run after
+      // it. Rewriting urls on that discarded tree leaves the emitted CSS
+      // pointing at the original source-relative paths.
+      result.root.walkDecls((declaration) => {
         const importer = declaration.source?.input.file
         if (!importer) {
           opts.logger.warnOnce(
diff --git a/playground/css/__tests__/css.spec.ts b/playground/css/__tests__/css.spec.ts
index aa0fe2e4914c59..7d4a1f56e8d751 100644
--- a/playground/css/__tests__/css.spec.ts
+++ b/playground/css/__tests__/css.spec.ts
@@ -12,3 +12,20 @@ test('postcss plugin that injects url() at OnceExit', async () => {
     isBundled ? /base64/ : '/injected-source/injected-bg.png',
   )
 })
+
+// a plugin that reassigns `result.root` (like postcss-lightningcss or
+// @tailwindcss/vite) discards the tree Vite's url rewriter walked, so the
+// rewritten urls must be read back off the live root
+// (https://github.com/vitejs/vite/issues/23348)
+test('postcss plugin that replaces the root at OnceExit', async () => {
+  await page.goto(viteTestUrl)
+  const replaced = await page.waitForSelector('.replace-root')
+  // the raw `./replaced-bg.png` must not survive: it is relative to the
+  // source file, not to wherever the emitted stylesheet ends up. The hash
+  // (bundled) and the source directory (served) are what prove it was rebased
+  expect(await getBg(replaced)).toMatch(
+    isBundled
+      ? /\/replaced-bg-[-\w]+\.png/
+      : '/replace-root-source/replaced-bg.png',
+  )
+})
diff --git a/playground/css/index.html b/playground/css/index.html
index 4231a85e8722d6..a1e8df99059f41 100644
--- a/playground/css/index.html
+++ b/playground/css/index.html
@@ -27,6 +27,10 @@ <h1>CSS</h1>
   <p class="inject-url-once-exit">
     PostCSS plugin injecting at OnceExit: this should have a background image
   </p>
+  <p class="replace-root">
+    PostCSS plugin replacing the root at OnceExit: this should have a background
+    image
+  </p>
 
   <p class="sass">SASS: This should be orange</p>
   <p class="sass-at-import">
diff --git a/playground/css/main.js b/playground/css/main.js
index f278820595ca1b..6ea9f10ae89008 100644
--- a/playground/css/main.js
+++ b/playground/css/main.js
@@ -7,6 +7,7 @@ import './less-plugin.less'
 import './stylus.styl'
 import './manual-chunk.css'
 import './postcss-inject-url.css'
+import './postcss-replace-root.css'
 
 import urlCss from './url-imported.css?url'
 appendLinkStylesheet(urlCss)
diff --git a/playground/css/postcss-replace-root.css b/playground/css/postcss-replace-root.css
new file mode 100644
index 00000000000000..6459aa716c8281
--- /dev/null
+++ b/playground/css/postcss-replace-root.css
@@ -0,0 +1 @@
+@replace-root;
diff --git a/playground/css/postcss.config.js b/playground/css/postcss.config.js
index 8198b58495166a..6a87dd906f457b 100644
--- a/playground/css/postcss.config.js
+++ b/playground/css/postcss.config.js
@@ -11,6 +11,7 @@ export default {
     testSourceInput,
     testInjectUrl,
     testInjectUrlOnceExit,
+    testReplaceRoot,
   ],
 }
 
@@ -116,3 +117,31 @@ function testInjectUrlOnceExit() {
   }
 }
 testInjectUrlOnceExit.postcss = true
+
+/**
+ * A plugin for testing url() rewriting when a plugin replaces the whole tree
+ * at OnceExit by reassigning `result.root` (like postcss-lightningcss or
+ * @tailwindcss/vite do).
+ */
+function testReplaceRoot() {
+  return {
+    postcssPlugin: 'replace-root',
+    OnceExit(root, { result, postcss }) {
+      if (!root.some((node) => node.name === 'replace-root')) return
+      // re-parse from scratch and hand back a brand new tree instead of
+      // mutating `root`, the way postcss-lightningcss and @tailwindcss/vite
+      // return their own output. `from` points at the source file so the
+      // relative url has something to be rebased against.
+      result.root = postcss.parse(
+        '.replace-root { background: url(./replaced-bg.png) }',
+        {
+          from: path.join(
+            import.meta.dirname,
+            'replace-root-source/replaced.css',
+          ),
+        },
+      )
+    },
+  }
+}
+testReplaceRoot.postcss = true
diff --git a/playground/css/replace-root-source/replaced-bg.png b/playground/css/replace-root-source/replaced-bg.png
new file mode 100644
index 00000000000000..eb9f67ae59d62f
Binary files /dev/null and b/playground/css/replace-root-source/replaced-bg.png differ