diff --git a/packages/vite/src/client/client.ts b/packages/vite/src/client/client.ts
index 1fc8c2b522fdb3..6e6694ec7b85dd 100644
--- a/packages/vite/src/client/client.ts
+++ b/packages/vite/src/client/client.ts
@@ -514,14 +514,64 @@ if ('document' in globalThis) {
     })
 }
 
-// all css imports should be inserted at the same position
-// because after build it will be a single css file
-let lastInsertedStyle: HTMLStyleElement | undefined
+// Track which CSS files have been successfully inserted
+const insertedCSS = new Set<string>()
+// Queue for CSS files waiting for their dependencies
+const pendingCSS = new Map<string, { css: string; deps: string[] }>()
 
-export function updateStyle(id: string, content: string): void {
+/**
+ * Track the last inserted Vite CSS for maintaining arrival order.
+ * Reset via setTimeout to separate chunks loaded at different times.
+ */
+let lastInsertedViteCSS: HTMLStyleElement | null = null
+
+/**
+ * Update or insert a CSS style element with dependency-aware ordering.
+ *
+ * In dev mode, CSS files may load in arbitrary order due to parallel dynamic imports.
+ * This function ensures CSS is inserted in dependency order (dependencies before dependents)
+ * to match the build mode behavior.
+ *
+ * Algorithm:
+ * 1. Check if all dependencies have been inserted
+ * 2. If not ready, queue this CSS and wait
+ * 3. If ready, insert CSS after its dependencies in the DOM
+ * 4. Mark as inserted and process any pending CSS that was waiting for this one
+ *
+ * @param id - Unique identifier for the CSS module
+ * @param content - The CSS content to insert
+ * @param deps - Array of CSS module IDs this CSS depends on (should load before this)
+ */
+export function updateStyle(
+  id: string,
+  content: string,
+  deps: string[] = [],
+): void {
   if (linkSheetsMap.has(id)) return
 
   let style = sheetsMap.get(id)
+
+  // Check if we're updating existing style (HMR)
+  const isUpdate = !!style
+
+  if (isUpdate) {
+    // For HMR updates, just update content and keep position
+    style!.textContent = content
+    sheetsMap.set(id, style!)
+    return
+  }
+
+  // New CSS insertion - check dependencies
+  const depsReady = deps.every((depId) => insertedCSS.has(depId))
+
+  if (!depsReady) {
+    // Dependencies not ready - queue this CSS for later
+    // Don't create element yet - it will be created when dependencies are ready
+    pendingCSS.set(id, { css: content, deps })
+    return
+  }
+
+  // Dependencies are ready - insert CSS
   if (!style) {
     style = document.createElement('style')
     style.setAttribute('type', 'text/css')
@@ -530,23 +580,94 @@ export function updateStyle(id: string, content: string): void {
     if (cspNonce) {
       style.setAttribute('nonce', cspNonce)
     }
+  }
 
-    if (!lastInsertedStyle) {
-      document.head.appendChild(style)
-
-      // reset lastInsertedStyle after async
-      // because dynamically imported css will be split into a different file
-      setTimeout(() => {
-        lastInsertedStyle = undefined
-      }, 0)
-    } else {
-      lastInsertedStyle.insertAdjacentElement('afterend', style)
+  // Find the insertion point - after the last dependency
+  let insertAfter: HTMLStyleElement | null = null
+
+  for (const depId of deps) {
+    const depStyle = sheetsMap.get(depId)
+    if (depStyle) {
+      // Find the last dependency in DOM order
+      if (
+        !insertAfter ||
+        depStyle.compareDocumentPosition(insertAfter) &
+          Node.DOCUMENT_POSITION_FOLLOWING
+      ) {
+        insertAfter = depStyle
+      }
     }
-    lastInsertedStyle = style
+  }
+
+  // Insert the style element based on dependencies
+  if (insertAfter) {
+    // Has dependencies - insert right after the last dependency
+    // For static imports, this maintains proper cascade
+    // For dynamic imports, dependencies are likely at the end, so this puts it at end too
+    insertAfter.insertAdjacentElement('afterend', style)
+  } else if (deps.length > 0) {
+    // Has dependencies but none found - append to end as fallback
+    document.head.appendChild(style)
+  } else if (lastInsertedViteCSS && lastInsertedViteCSS.parentNode) {
+    // No dependencies - use arrival order
+    lastInsertedViteCSS.insertAdjacentElement('afterend', style)
   } else {
-    style.textContent = content
+    // First CSS or reset - append to end
+    // This ensures it can override any existing styles
+    document.head.appendChild(style)
   }
+
   sheetsMap.set(id, style)
+  insertedCSS.add(id)
+
+  // Track for arrival-order insertion
+  lastInsertedViteCSS = style
+
+  // Reset tracking after async to prevent cross-chunk chaining
+  if (deps.length === 0) {
+    setTimeout(() => {
+      if (lastInsertedViteCSS === style) {
+        lastInsertedViteCSS = null
+      }
+    }, 0)
+  }
+
+  // Process any pending CSS that was waiting for this one
+  processPendingCSS()
+}
+
+/**
+ * Process pending CSS that may now be ready to insert.
+ * Called after a CSS file is successfully inserted.
+ *
+ * This uses a loop to handle transitive dependencies - CSS that becomes ready
+ * after we insert CSS that was itself waiting. Without this, we could have
+ * deadlocks where CSS is stuck waiting forever.
+ */
+function processPendingCSS(): void {
+  // Keep processing until no more CSS becomes ready
+  // This handles chains: A waits for B, B waits for C, C just loaded
+  let processedAny = true
+
+  while (processedAny) {
+    processedAny = false
+    const toProcess: Array<[string, { css: string; deps: string[] }]> = []
+
+    // Find all pending CSS whose dependencies are now satisfied
+    for (const [id, { css, deps }] of pendingCSS.entries()) {
+      const allDepsReady = deps.every((depId) => insertedCSS.has(depId))
+      if (allDepsReady) {
+        toProcess.push([id, { css, deps }])
+        processedAny = true
+      }
+    }
+
+    // Insert all CSS that became ready in this iteration
+    for (const [id, { css, deps }] of toProcess) {
+      pendingCSS.delete(id)
+      updateStyle(id, css, deps)
+    }
+  }
 }
 
 export function removeStyle(id: string): void {
@@ -565,9 +686,15 @@ export function removeStyle(id: string): void {
   }
   const style = sheetsMap.get(id)
   if (style) {
+    // If we're removing the last inserted CSS, clear the tracker
+    if (style === lastInsertedViteCSS) {
+      lastInsertedViteCSS = null
+    }
     document.head.removeChild(style)
     sheetsMap.delete(id)
+    insertedCSS.delete(id)
   }
+  pendingCSS.delete(id)
 }
 
 export function createHotContext(ownerPath: string): ViteHotContext {
diff --git a/packages/vite/src/node/plugins/css.ts b/packages/vite/src/node/plugins/css.ts
index b80696ae6e4784..44e70d902c4020 100644
--- a/packages/vite/src/node/plugins/css.ts
+++ b/packages/vite/src/node/plugins/css.ts
@@ -451,6 +451,79 @@ export function cssPlugin(config: ResolvedConfig): Plugin {
   }
 }
 
+/**
+ * Calculate CSS dependencies for a given CSS module in dev mode.
+ *
+ * This function traverses the module graph to find all CSS files that should
+ * be loaded before the given CSS file, based on the dependency chain of JS modules.
+ *
+ * Algorithm:
+ * 1. Start with the CSS module
+ * 2. Find all JS modules that import this CSS (importers)
+ * 3. For each JS importer, look at what other modules it imports
+ * 4. Collect all CSS files from those imports (these are dependencies)
+ * 5. Recursively process JS modules to handle transitive dependencies
+ * 6. Track visited JS modules to prevent infinite loops (circular dependencies)
+ * 7. Return deduplicated list of CSS dependency IDs in deterministic order
+ *
+ * Example:
+ *   async-1.css is imported by async-1.js
+ *   async-1.js also imports base.js
+ *   base.js imports base.css
+ *   → Result: async-1.css depends on base.css
+ *
+ * @param cssModuleId - The ID of the CSS module to find dependencies for
+ * @param moduleGraph - The dev environment module graph
+ * @returns Array of CSS module IDs that should load before this CSS
+ */
+function getCssDependencies(
+  cssModuleId: string,
+  moduleGraph: import('../server/moduleGraph').EnvironmentModuleGraph,
+): string[] {
+  const cssModule = moduleGraph.getModuleById(cssModuleId)
+  if (!cssModule) {
+    return []
+  }
+
+  const cssDeps = new Set<string>()
+  const visitedJsModules = new Set<EnvironmentModuleNode>()
+
+  /**
+   * Recursively collect CSS dependencies from a JS module's imports
+   */
+  function collectDepsFromJsModule(jsModule: EnvironmentModuleNode) {
+    // Prevent infinite loops from circular JS dependencies
+    if (visitedJsModules.has(jsModule)) {
+      return
+    }
+    visitedJsModules.add(jsModule)
+
+    // Look at what this JS module imports
+    for (const imported of jsModule.importedModules) {
+      if (imported.type === 'css') {
+        // Found a CSS dependency (but not the original CSS file itself)
+        if (imported.id && imported.id !== cssModuleId) {
+          cssDeps.add(imported.id)
+        }
+      } else if (imported.type === 'js') {
+        // Recursively check what this JS module imports
+        collectDepsFromJsModule(imported)
+      }
+    }
+  }
+
+  // Start from all JS modules that import this CSS file
+  for (const importer of cssModule.importers) {
+    if (importer.type === 'js') {
+      collectDepsFromJsModule(importer)
+    }
+  }
+
+  // Convert Set to Array for deterministic ordering
+  // Sets preserve insertion order in ES2015+
+  return Array.from(cssDeps)
+}
+
 /**
  * Plugin applied after user plugins
  */
@@ -587,13 +660,20 @@ export function cssPostPlugin(config: ResolvedConfig): Plugin {
           }
 
           const cssContent = await getContentWithSourcemap(css)
+
+          // Calculate CSS dependencies for proper ordering in dev mode
+          // This ensures CSS loads in the same order as build mode
+          const { moduleGraph } = this.environment as DevEnvironment
+          const cssDeps = getCssDependencies(id, moduleGraph)
+
           const code = [
             `import { updateStyle as __vite__updateStyle, removeStyle as __vite__removeStyle } from ${JSON.stringify(
               path.posix.join(config.base, CLIENT_PUBLIC_PATH),
             )}`,
             `const __vite__id = ${JSON.stringify(id)}`,
             `const __vite__css = ${JSON.stringify(cssContent)}`,
-            `__vite__updateStyle(__vite__id, __vite__css)`,
+            `const __vite__deps = ${JSON.stringify(cssDeps)}`,
+            `__vite__updateStyle(__vite__id, __vite__css, __vite__deps)`,
             // css modules exports change on edit so it can't self accept
             `${modulesCode || 'import.meta.hot.accept()'}`,
             `import.meta.hot.prune(() => __vite__removeStyle(__vite__id))`,
diff --git a/playground/css/__tests__/tests.ts b/playground/css/__tests__/tests.ts
index 68ff600a39c002..42518e1cbeaf32 100644
--- a/playground/css/__tests__/tests.ts
+++ b/playground/css/__tests__/tests.ts
@@ -512,6 +512,28 @@ export const tests = (isLightningCSS: boolean) => {
     await expect.poll(() => getColor('.modules-pink')).toBe('pink')
   })
 
+  // Test for issue #3924: CSS injection order with diamond dependencies
+  test('async css order with diamond dependencies', async () => {
+    // Diamond dependency: main -> [chunk-a, chunk-b] -> shared-base
+    // Expected order: shared-base.css, chunk-a.css, chunk-b.css
+    // chunk-b.css should win (.diamond-test { color: green; background: yellow })
+    await expect.poll(() => getColor('.diamond-test')).toBe('green')
+    await expect.poll(() => getBgColor('.diamond-test')).toBe('yellow')
+  })
+
+  // Test for issue #9278: Shared function with global CSS before module CSS
+  test('async css order with shared dependency and global CSS', async () => {
+    // Both blue.js and black.js import make-text.js (shared dependency)
+    // Both import hotpink.css before their own module CSS
+    // Expected: hotpink.css should load first, then blue/black module CSS should win
+    // The elements have both .hotpink and their module class
+    const blueEl = await page.locator('text=async blue').first()
+    const blackEl = await page.locator('text=async black').first()
+
+    await expect.poll(() => getColor(blueEl)).toBe('blue')
+    await expect.poll(() => getColor(blackEl)).toBe('black')
+  })
+
   test('@import scss', async () => {
     expect(await getColor('.at-import-scss')).toBe('red')
   })
diff --git a/playground/css/async/black.js b/playground/css/async/black.js
new file mode 100644
index 00000000000000..8d72db8b2f0e63
--- /dev/null
+++ b/playground/css/async/black.js
@@ -0,0 +1,5 @@
+import { makeText } from './make-text'
+import './hotpink.css'
+import styles from './black.module.css'
+
+makeText(styles['black-module'], 'async black')
diff --git a/playground/css/async/black.module.css b/playground/css/async/black.module.css
new file mode 100644
index 00000000000000..8a609488859d8a
--- /dev/null
+++ b/playground/css/async/black.module.css
@@ -0,0 +1,3 @@
+.black-module {
+  color: black;
+}
diff --git a/playground/css/async/blue.js b/playground/css/async/blue.js
new file mode 100644
index 00000000000000..a0fc833168cb9b
--- /dev/null
+++ b/playground/css/async/blue.js
@@ -0,0 +1,5 @@
+import { makeText } from './make-text'
+import './hotpink.css'
+import styles from './blue.module.css'
+
+makeText(styles['blue-module'], 'async blue')
diff --git a/playground/css/async/blue.module.css b/playground/css/async/blue.module.css
new file mode 100644
index 00000000000000..cdbea06a0ba2b0
--- /dev/null
+++ b/playground/css/async/blue.module.css
@@ -0,0 +1,3 @@
+.blue-module {
+  color: blue;
+}
diff --git a/playground/css/async/chunk-a.css b/playground/css/async/chunk-a.css
new file mode 100644
index 00000000000000..b39fe617d748dd
--- /dev/null
+++ b/playground/css/async/chunk-a.css
@@ -0,0 +1,5 @@
+/* Chunk A depends on shared-base */
+/* This should come AFTER shared-base.css */
+.diamond-test {
+  color: blue;
+}
diff --git a/playground/css/async/chunk-a.js b/playground/css/async/chunk-a.js
new file mode 100644
index 00000000000000..fda6d621c7e006
--- /dev/null
+++ b/playground/css/async/chunk-a.js
@@ -0,0 +1,8 @@
+import { initSharedBase } from './shared-base'
+import './chunk-a.css'
+
+initSharedBase()
+
+export function initChunkA() {
+  console.log('[chunk-a] initialized')
+}
diff --git a/playground/css/async/chunk-b.css b/playground/css/async/chunk-b.css
new file mode 100644
index 00000000000000..8e1c4d3db45388
--- /dev/null
+++ b/playground/css/async/chunk-b.css
@@ -0,0 +1,6 @@
+/* Chunk B also depends on shared-base */
+/* This should come AFTER shared-base.css AND chunk-a.css */
+.diamond-test {
+  color: green;
+  background: yellow;
+}
diff --git a/playground/css/async/chunk-b.js b/playground/css/async/chunk-b.js
new file mode 100644
index 00000000000000..28aedcfb5830a3
--- /dev/null
+++ b/playground/css/async/chunk-b.js
@@ -0,0 +1,16 @@
+import { initSharedBase } from './shared-base'
+import { initChunkA } from './chunk-a'
+import './chunk-b.css'
+
+initSharedBase()
+initChunkA()
+
+export function initChunkB() {
+  console.log('[chunk-b] initialized')
+
+  // Create test element
+  const div = document.createElement('div')
+  div.className = 'diamond-test'
+  div.textContent = 'Diamond Dependency Test'
+  document.body.appendChild(div)
+}
diff --git a/playground/css/async/diamond.js b/playground/css/async/diamond.js
new file mode 100644
index 00000000000000..3d775bbf5cbcf0
--- /dev/null
+++ b/playground/css/async/diamond.js
@@ -0,0 +1,16 @@
+// This creates a diamond dependency:
+// main (this file)
+//   -> chunk-a -> shared-base
+//   -> chunk-b -> shared-base
+//               -> chunk-a -> shared-base
+//
+// Expected CSS order: shared-base.css, chunk-a.css, chunk-b.css
+// Expected final color: green (from chunk-b)
+// Expected final background: yellow (from chunk-b)
+
+Promise.all([import('./chunk-a.js'), import('./chunk-b.js')]).then(
+  ([modA, modB]) => {
+    modA.initChunkA()
+    modB.initChunkB()
+  },
+)
diff --git a/playground/css/async/hotpink.css b/playground/css/async/hotpink.css
new file mode 100644
index 00000000000000..a79d1ee0de1f48
--- /dev/null
+++ b/playground/css/async/hotpink.css
@@ -0,0 +1,3 @@
+.hotpink {
+  color: hotpink;
+}
diff --git a/playground/css/async/index.js b/playground/css/async/index.js
index 20d6975ab9d23a..5d2719c160ae9d 100644
--- a/playground/css/async/index.js
+++ b/playground/css/async/index.js
@@ -1,3 +1,6 @@
 import('./async-1.js')
 import('./async-2.js')
 import('./async-3.js')
+import('./diamond.js')
+import('./blue.js')
+import('./black.js')
diff --git a/playground/css/async/make-text.js b/playground/css/async/make-text.js
new file mode 100644
index 00000000000000..dfd84ce8d7552c
--- /dev/null
+++ b/playground/css/async/make-text.js
@@ -0,0 +1,6 @@
+export function makeText(className, content) {
+  const div = document.createElement('div')
+  div.className = `base hotpink ${className}`
+  document.body.appendChild(div)
+  div.textContent = `${content} ${getComputedStyle(div).color}`
+}
diff --git a/playground/css/async/shared-base.css b/playground/css/async/shared-base.css
new file mode 100644
index 00000000000000..7351de2570eaa6
--- /dev/null
+++ b/playground/css/async/shared-base.css
@@ -0,0 +1,6 @@
+/* This CSS is imported by both chunk-a and chunk-b */
+/* In correct order, chunk-b's CSS should override this */
+.diamond-test {
+  color: red;
+  background: black;
+}
diff --git a/playground/css/async/shared-base.js b/playground/css/async/shared-base.js
new file mode 100644
index 00000000000000..ab07f9f5af342d
--- /dev/null
+++ b/playground/css/async/shared-base.js
@@ -0,0 +1,5 @@
+import './shared-base.css'
+
+export function initSharedBase() {
+  console.log('[shared-base] initialized')
+}