diff --git a/packages/angular/build/src/builders/application/tests/behavior/rebuild-global_styles_spec.ts b/packages/angular/build/src/builders/application/tests/behavior/rebuild-global_styles_spec.ts
index 2de5c5f229ca..3cb5d41de1fe 100644
--- a/packages/angular/build/src/builders/application/tests/behavior/rebuild-global_styles_spec.ts
+++ b/packages/angular/build/src/builders/application/tests/behavior/rebuild-global_styles_spec.ts
@@ -198,6 +198,68 @@ describeBuilder(buildApplication, APPLICATION_BUILDER_INFO, (harness) => {
       );
     });
 
+    it('rebuilds PostCSS stylesheet when a file is added to a plugin directory dependency', async () => {
+      harness.useTarget('build', {
+        ...BASE_OPTIONS,
+        watch: true,
+        styles: ['src/styles.css'],
+      });
+
+      // Emits a class for each source file, similar to Tailwind CSS v4 content scanning
+      await harness.writeFile(
+        'test-plugin.js',
+        `
+        const fs = require('fs');
+        const path = require('path');
+        module.exports = () => {
+          return {
+            postcssPlugin: 'test-plugin',
+            Once(root, { result }) {
+              const dir = path.join(path.dirname(root.source.input.file), 'sources');
+              result.messages.push({
+                type: 'dir-dependency',
+                dir,
+                glob: '**/*.txt',
+              });
+              for (const file of fs.readdirSync(dir, { recursive: true })) {
+                if (file.endsWith('.txt')) {
+                  const name = fs.readFileSync(path.join(dir, file), 'utf-8').trim();
+                  root.append('.' + name + ' { color: red; }');
+                }
+              }
+            },
+          };
+        };
+        module.exports.postcss = true;
+        `,
+      );
+      await harness.writeFile(
+        '.postcssrc.json',
+        JSON.stringify({
+          plugins: {
+            './test-plugin.js': {},
+          },
+        }),
+      );
+      await harness.writeFile('src/styles.css', '/* base */');
+      await harness.writeFile('src/sources/foo/a.txt', 'foo-class');
+
+      await harness.executeWithCases([
+        async ({ result }) => {
+          expect(result?.success).toBe(true);
+          harness.expectFile('dist/browser/styles.css').content.toContain('.foo-class');
+          harness.expectFile('dist/browser/styles.css').content.not.toContain('.bar-class');
+
+          await harness.writeFile('src/sources/bar/b.txt', 'bar-class');
+        },
+        ({ result }) => {
+          expect(result?.success).toBe(true);
+          harness.expectFile('dist/browser/styles.css').content.toContain('.foo-class');
+          harness.expectFile('dist/browser/styles.css').content.toContain('.bar-class');
+        },
+      ]);
+    });
+
     it('rebuilds PostCSS stylesheet after CSS syntax error on initial build from import', async () => {
       harness.useTarget('build', {
         ...BASE_OPTIONS,
diff --git a/packages/angular/build/src/tools/esbuild/load-result-cache.ts b/packages/angular/build/src/tools/esbuild/load-result-cache.ts
index 402069cff1a5..c413f9375778 100644
--- a/packages/angular/build/src/tools/esbuild/load-result-cache.ts
+++ b/packages/angular/build/src/tools/esbuild/load-result-cache.ts
@@ -7,7 +7,7 @@
  */
 
 import type { OnLoadResult, PluginBuild } from 'esbuild';
-import { normalize } from 'node:path';
+import { dirname, normalize } from 'node:path';
 
 export interface LoadResultCache {
   get(path: string): OnLoadResult | Promise<OnLoadResult | undefined> | undefined;
@@ -108,16 +108,27 @@ export class MemoryLoadResultCache implements LoadResultCache {
   }
 
   invalidate(path: string): boolean {
-    const affectedPaths = this.#fileDependencies.get(path);
-    if (!affectedPaths) {
-      return false;
-    }
+    let invalid = false;
+
+    // Check parent directories to support directory dependencies (PostCSS `dir-dependency`)
+    let current = normalize(path);
+    while (true) {
+      const affectedPaths = this.#fileDependencies.get(current);
+      if (affectedPaths) {
+        for (const affected of affectedPaths) {
+          this.#loadResults.delete(affected);
+        }
+        invalid = true;
+      }
 
-    for (const affected of affectedPaths) {
-      this.#loadResults.delete(affected);
+      const parent = dirname(current);
+      if (parent === current) {
+        break;
+      }
+      current = parent;
     }
 
-    return true;
+    return invalid;
   }
 
   get watchFiles(): string[] {
diff --git a/packages/angular/build/src/tools/esbuild/load-result-cache_spec.ts b/packages/angular/build/src/tools/esbuild/load-result-cache_spec.ts
index 8a8682beed61..876308f94512 100644
--- a/packages/angular/build/src/tools/esbuild/load-result-cache_spec.ts
+++ b/packages/angular/build/src/tools/esbuild/load-result-cache_spec.ts
@@ -55,6 +55,22 @@ describe('MemoryLoadResultCache', () => {
     expect(cache.get('file:/test/styles.css')).toBeUndefined();
   });
 
+  it('should invalidate cached results when a file inside a dependency directory changes', async () => {
+    const result = {
+      contents: 'body { color: red; }',
+      loader: 'css' as const,
+      watchFiles: ['/test/styles.css', '/test/src'],
+    };
+
+    await cache.put('file:/test/styles.css', result);
+
+    expect(cache.invalidate('/test/other/a.ts')).toBeFalse();
+    expect(cache.get('file:/test/styles.css')).toBe(result);
+
+    expect(cache.invalidate('/test/src/app/new/a.ts')).toBeTrue();
+    expect(cache.get('file:/test/styles.css')).toBeUndefined();
+  });
+
   it('should preserve previous watch files when caching an error result', async () => {
     const successResult = {
       contents: 'body { color: red; }',
diff --git a/packages/angular/build/src/tools/esbuild/stylesheets/stylesheet-plugin-factory.ts b/packages/angular/build/src/tools/esbuild/stylesheets/stylesheet-plugin-factory.ts
index 79337fe1652e..b3f320146510 100644
--- a/packages/angular/build/src/tools/esbuild/stylesheets/stylesheet-plugin-factory.ts
+++ b/packages/angular/build/src/tools/esbuild/stylesheets/stylesheet-plugin-factory.ts
@@ -401,6 +401,8 @@ async function compileString(
         typeof resultMessage['glob'] === 'string'
       ) {
         loadResult.watchFiles ??= [];
+        // Watch the directory itself so files added or moved into it later also cause a rebuild
+        loadResult.watchFiles.push(resultMessage['dir']);
         const dependencies = await glob(resultMessage['glob'], {
           absolute: true,
           cwd: resultMessage['dir'],