diff --git a/packages/vite/src/node/plugins/importAnalysisBuild.ts b/packages/vite/src/node/plugins/importAnalysisBuild.ts
index e5a07630355cdb..ae84f7eb6d0a6e 100644
--- a/packages/vite/src/node/plugins/importAnalysisBuild.ts
+++ b/packages/vite/src/node/plugins/importAnalysisBuild.ts
@@ -369,6 +369,36 @@ export function buildImportAnalysisPlugin(config: ResolvedConfig): Plugin[] {
           }
 
           if (imports.length) {
+            // Each import is wrapped as `__vitePreload(factory, __VITE_PRELOAD__)`, so its
+            // marker comes right after it. Nested imports nest the wrappers — in
+            // `import('a').then(() => import('b'))` b's marker ends up before a's — so imports
+            // and markers form balanced brackets. Pairing each import with the next marker
+            // would give b's marker to both and lose a's CSS to `void 0` (#22700); instead,
+            // match them with a stack in one pass: each marker closes the innermost open import.
+            const importMarkerPos = new Array<number>(imports.length).fill(-1)
+            const openImports: number[] = []
+            let nextImport = 0
+            let markerStartPos = findPreloadMarker(code, imports[0].e)
+            while (markerStartPos !== -1) {
+              while (
+                nextImport < imports.length &&
+                imports[nextImport].e <= markerStartPos
+              ) {
+                openImports.push(nextImport++)
+              }
+              if (openImports.length) {
+                importMarkerPos[openImports.pop()!] = markerStartPos
+              }
+              markerStartPos = findPreloadMarker(
+                code,
+                markerStartPos + preloadMarker.length,
+              )
+            }
+            // #3051: a lone import whose marker isn't placed after it pairs with the only marker
+            if (imports.length === 1 && importMarkerPos[0] === -1) {
+              importMarkerPos[0] = findPreloadMarker(code)
+            }
+
             for (let index = 0; index < imports.length; index++) {
               // To handle escape sequences in specifier strings, the .n field will be provided where possible.
               const {
@@ -438,11 +468,7 @@ export function buildImportAnalysisPlugin(config: ResolvedConfig): Plugin[] {
                 addDeps(normalizedFile)
               }
 
-              let markerStartPos = findPreloadMarker(code, end)
-              // fix issue #3051
-              if (markerStartPos === -1 && imports.length === 1) {
-                markerStartPos = findPreloadMarker(code)
-              }
+              const markerStartPos = importMarkerPos[index]
 
               if (markerStartPos > 0) {
                 // the dep list includes the main chunk, so only need to reload when there are actual other deps.
diff --git a/playground/dynamic-import/__tests__/dynamic-import.spec.ts b/playground/dynamic-import/__tests__/dynamic-import.spec.ts
index 384f4190295f46..76589d94b493fb 100644
--- a/playground/dynamic-import/__tests__/dynamic-import.spec.ts
+++ b/playground/dynamic-import/__tests__/dynamic-import.spec.ts
@@ -135,6 +135,44 @@ test('should work with load ../ and contain itself directory', async () => {
     .toMatch('dynamic-import-nested-self-content')
 })
 
+// #22700: nested `import('a').then(() => import('b'))` where `a` has a CSS
+// side-effect dep — the outer import's CSS must still be loaded in build output
+test('should load css of nested dynamic import', async () => {
+  await expect
+    .poll(() => page.textContent('.then-css-outer'))
+    .toMatch('then-css-outer')
+  await expect.poll(() => getColor('.then-css-outer')).toBe('red')
+  await expect
+    .poll(() => page.textContent('.then-css-inner'))
+    .toMatch('then-css-inner')
+  await expect.poll(() => getColor('.then-css-inner')).toBe('green')
+})
+
+// #22721: each nested dynamic import must preload its OWN chunk's css. The inner
+// import is immediately followed by its own `__vite__mapDeps(...)` (its `.then`
+// callback contains no further import, so the first dep list after it is its
+// own), so we read that list back and confirm it resolves to the inner css. A
+// pairing that walks imports front-to-back and skips already-claimed markers
+// swaps the lists, putting the outer chunk's css here instead.
+test.runIf(isBuild)(
+  'should preload its own css for a nested dynamic import',
+  () => {
+    const js = findAssetFile(/index-[-\w]{8}\.js$/) ?? ''
+    const depTable = js.match(/m\.f=(\[[^\]]*\])/)
+    const innerCall = js.match(
+      /import\([^)]*\binner-[-\w]+\.js[^)]*\)[\s\S]*?__vite__mapDeps\(\[([\d,]+)\]\)/,
+    )
+    expect(depTable, 'preload dep table not found').not.toBeNull()
+    expect(innerCall, 'inner import preload call not found').not.toBeNull()
+    const files: string[] = JSON.parse(depTable![1])
+    const innerPreloads = innerCall![1].split(',').map((i) => files[Number(i)])
+    expect(innerPreloads.some((f) => /\binner-[-\w]+\.css$/.test(f))).toBe(true)
+    expect(innerPreloads.some((f) => /\bouter-[-\w]+\.css$/.test(f))).toBe(
+      false,
+    )
+  },
+)
+
 test('should work a load path that contains parentheses.', async () => {
   await expect
     .poll(() =>
diff --git a/playground/dynamic-import/index.html b/playground/dynamic-import/index.html
index 1289efc3e1ac4e..a5a0832ba5c299 100644
--- a/playground/dynamic-import/index.html
+++ b/playground/dynamic-import/index.html
@@ -45,6 +45,9 @@
 
 <div class="dynamic-import-nested-self"></div>
 
+<div class="then-css-outer">todo</div>
+<div class="then-css-inner">todo</div>
+
 <script type="module" src="./nested/index.js"></script>
 <script type="module" src="./(app)/nest/index.js"></script>
 <style>
diff --git a/playground/dynamic-import/nested/index.js b/playground/dynamic-import/nested/index.js
index 6520e1f5a51bb8..c6e9ee406122e2 100644
--- a/playground/dynamic-import/nested/index.js
+++ b/playground/dynamic-import/nested/index.js
@@ -201,4 +201,13 @@ import(`../nested/static.js`).then((mod) => {
   text('.dynamic-import-static', mod.self)
 })
 
+// #22700: in a nested `import().then(() => import())`, the outer import's CSS
+// dep used to be dropped to `void 0` in the build output, orphaning the CSS.
+import('./then-css/outer.js').then((outerMod) => {
+  text('.then-css-outer', outerMod.outer)
+  return import('./then-css/inner.js').then((innerMod) => {
+    text('.then-css-inner', innerMod.inner)
+  })
+})
+
 console.log('index.js')
diff --git a/playground/dynamic-import/nested/then-css/inner.css b/playground/dynamic-import/nested/then-css/inner.css
new file mode 100644
index 00000000000000..9855e17deed416
--- /dev/null
+++ b/playground/dynamic-import/nested/then-css/inner.css
@@ -0,0 +1,3 @@
+.then-css-inner {
+  color: #008000;
+}
diff --git a/playground/dynamic-import/nested/then-css/inner.js b/playground/dynamic-import/nested/then-css/inner.js
new file mode 100644
index 00000000000000..01624aa992e57a
--- /dev/null
+++ b/playground/dynamic-import/nested/then-css/inner.js
@@ -0,0 +1,2 @@
+import './inner.css'
+export const inner = 'then-css-inner'
diff --git a/playground/dynamic-import/nested/then-css/outer.css b/playground/dynamic-import/nested/then-css/outer.css
new file mode 100644
index 00000000000000..f829bca5b01a5a
--- /dev/null
+++ b/playground/dynamic-import/nested/then-css/outer.css
@@ -0,0 +1,3 @@
+.then-css-outer {
+  color: #ff0000;
+}
diff --git a/playground/dynamic-import/nested/then-css/outer.js b/playground/dynamic-import/nested/then-css/outer.js
new file mode 100644
index 00000000000000..4e1516b996795a
--- /dev/null
+++ b/playground/dynamic-import/nested/then-css/outer.js
@@ -0,0 +1,2 @@
+import './outer.css'
+export const outer = 'then-css-outer'