diff --git a/e2e/react/src/react.test.ts b/e2e/react/src/react.test.ts
index c877b86a44..043bf20b1f 100644
--- a/e2e/react/src/react.test.ts
+++ b/e2e/react/src/react.test.ts
@@ -68,6 +68,8 @@ describe('React Applications', () => {
       const libName = uniq('lib');
       const libWithNoComponents = uniq('lib');
       const logoSvg = readFileSync(join(__dirname, 'logo.svg')).toString();
+      const blueSvg = `<?xml version="1.0"?><svg xmlns="http://www.w3.org/2000/svg" version="1.2" baseProfile="tiny" viewBox="0 0 30 30"><rect x="10" y="10" width="10" height="10" fill="blue"/></svg>`;
+      const redSvg = `<?xml version="1.0"?><svg xmlns="http://www.w3.org/2000/svg" version="1.2" baseProfile="tiny" viewBox="0 0 30 30"><rect x="10" y="10" width="10" height="10" fill="red"/></svg>`;
 
       runCLI(
         `generate @nx/react:app ${appName} --style=css --bundler=webpack --no-interactive --skipFormat`
@@ -92,11 +94,15 @@ describe('React Applications', () => {
       `
       );
 
+      updateFile(`apps/${appName}/src/app/blue/img.svg`, blueSvg); // ensure that same filenames do not conflict
+      updateFile(`apps/${appName}/src/app/red/img.svg`, redSvg); // ensure that same filenames do not conflict
       updateFile(`apps/${appName}/src/app/logo.svg`, logoSvg);
       updateFile(
         `apps/${appName}/src/app/app.tsx`,
         `
         import { ReactComponent as Logo } from './logo.svg';
+        import blue from './blue/img.svg';
+        import red from './red/img.svg';
         import logo from './logo.svg';
         import NxWelcome from './nx-welcome';
 
@@ -105,6 +111,8 @@ describe('React Applications', () => {
             <>
               <Logo />
               <img src={logo} alt="" />
+              <img src={blue} alt="" />
+              <img src={red} alt="" />
               <NxWelcome title="${appName}" />
             </>
           );
@@ -134,10 +142,7 @@ describe('React Applications', () => {
         checkSourceMap: true,
         checkStyles: true,
         checkLinter: true,
-        // TODO(caleb): Fix cypress tests
-        // /tmp/nx-e2e--1970-rQ4U0qBe6Nht/nx/proj1614306/dist/apps/app5172641/server/runtime.js:119
-        // if (typeof import.meta.url === "string") scriptUrl = import.meta.url
-        // SyntaxError: Cannot use 'import.meta' outside a module
+        // TODO(jack): check why Playwright tests are timing out in CI
         checkE2E: false,
       });
 
@@ -150,13 +155,10 @@ describe('React Applications', () => {
         checkSourceMap: false,
         checkStyles: false,
         checkLinter: false,
-        // TODO(caleb): Fix cypress tests
-        // /tmp/nx-e2e--1970-rQ4U0qBe6Nht/nx/proj1614306/dist/apps/app5172641/server/runtime.js:119
-        // if (typeof import.meta.url === "string") scriptUrl = import.meta.url
-        // SyntaxError: Cannot use 'import.meta' outside a module
+        // TODO(jack): check why Playwright tests are timing out in CI
         checkE2E: false,
       });
-    }, 500000);
+    }, 500_000);
 
     it('should generate app with routing', async () => {
       const appName = uniq('app');
@@ -532,7 +534,7 @@ async function testGeneratedApp(
 
   if (opts.checkE2E && runE2ETests()) {
     const e2eResults = runCLI(`e2e ${appName}-e2e`);
-    expect(e2eResults).toContain('All specs passed!');
+    expect(e2eResults).toContain('Successfully ran target e2e');
     expect(await killPorts()).toBeTruthy();
   }
 }
diff --git a/e2e/web/src/web.test.ts b/e2e/web/src/web.test.ts
index 46f1910b24..65dc1da459 100644
--- a/e2e/web/src/web.test.ts
+++ b/e2e/web/src/web.test.ts
@@ -5,6 +5,7 @@ import {
   createFile,
   isNotWindows,
   killPorts,
+  listFiles,
   newProject,
   readFile,
   runCLI,
@@ -79,22 +80,27 @@ describe('Web Components Applications', () => {
       'none'
     );
     runCLI(`build ${appName}`);
+    const images = listFiles(`dist/apps/${appName}`).filter((f) =>
+      f.endsWith('.png')
+    );
     checkFilesExist(
       `dist/apps/${appName}/index.html`,
       `dist/apps/${appName}/runtime.js`,
-      `dist/apps/${appName}/emitted.png`,
       `dist/apps/${appName}/main.js`,
       `dist/apps/${appName}/styles.css`
     );
-    checkFilesDoNotExist(`dist/apps/${appName}/inlined.png`);
+    expect(images.some((f) => f.startsWith('emitted.'))).toBe(true);
+    expect(images.some((f) => f.startsWith('inlined.'))).toBe(false);
 
     expect(readFile(`dist/apps/${appName}/main.js`)).toContain(
       'data:image/png;base64'
     );
     // Should not be a JS module but kept as a PNG
-    expect(readFile(`dist/apps/${appName}/emitted.png`)).not.toContain(
-      'export default'
-    );
+    expect(
+      readFile(
+        `dist/apps/${appName}/${images.find((f) => f.startsWith('emitted.'))}`
+      )
+    ).not.toContain('export default');
 
     expect(readFile(`dist/apps/${appName}/index.html`)).toContain(
       '<link rel="stylesheet" href="styles.css">'
diff --git a/packages/webpack/src/plugins/nx-webpack-plugin/lib/apply-web-config.ts b/packages/webpack/src/plugins/nx-webpack-plugin/lib/apply-web-config.ts
index 5dc11e9671..33a6e11d8f 100644
--- a/packages/webpack/src/plugins/nx-webpack-plugin/lib/apply-web-config.ts
+++ b/packages/webpack/src/plugins/nx-webpack-plugin/lib/apply-web-config.ts
@@ -332,6 +332,7 @@ export function applyWebConfig(
 
   config.output = {
     ...config.output,
+    assetModuleFilename: '[name].[contenthash:20][ext]',
     crossOriginLoading: options.subresourceIntegrity
       ? ('anonymous' as const)
       : (false as const),
@@ -404,9 +405,6 @@ export function applyWebConfig(
             maxSize: 10_000, // 10 kB
           },
         },
-        generator: {
-          filename: `[name]${hashFormat.file}[ext]`,
-        },
       },
       // SVG: same as image but we need to separate it so it can be swapped for SVGR in the React plugin.
       {
@@ -417,17 +415,11 @@ export function applyWebConfig(
             maxSize: 10_000, // 10 kB
           },
         },
-        generator: {
-          filename: `[name]${hashFormat.file}[ext]`,
-        },
       },
       // Fonts: Emit separate file and export the URL.
       {
         test: /\.(eot|otf|ttf|woff|woff2)$/,
         type: 'asset/resource',
-        generator: {
-          filename: `[name]${hashFormat.file}[ext]`,
-        },
       },
       ...rules,
     ],