diff --git a/packages/angular_devkit/build_angular/src/builders/dev-server/tests/options/proxy-config_spec.ts b/packages/angular_devkit/build_angular/src/builders/dev-server/tests/options/proxy-config_spec.ts
index 5ad6388497c0..31c11cdd11a9 100644
--- a/packages/angular_devkit/build_angular/src/builders/dev-server/tests/options/proxy-config_spec.ts
+++ b/packages/angular_devkit/build_angular/src/builders/dev-server/tests/options/proxy-config_spec.ts
@@ -6,7 +6,7 @@
  * found in the LICENSE file at https://angular.io/license
  */
 
-import * as http from 'http';
+import { createServer } from 'node:http';
 import { executeDevServer } from '../../index';
 import { executeOnceAndFetch } from '../execute-fetch';
 import { describeServeBuilder } from '../jasmine-helpers';
@@ -27,13 +27,10 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.json',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
-          'proxy.config.json': `{ "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }`,
+          'proxy.config.json': `{ "/api/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }`,
         });
 
         const { result, response } = await executeOnceAndFetch(harness, '/api/test');
@@ -41,7 +38,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -51,15 +48,12 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.json',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
           'proxy.config.json': `
             // JSON file with comments
-            { "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }
+            { "/api/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }
           `,
         });
 
@@ -68,7 +62,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -77,14 +71,10 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         ...BASE_OPTIONS,
         proxyConfig: 'proxy.config.js',
       });
-
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
-          'proxy.config.js': `module.exports = { "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }`,
+          'proxy.config.js': `module.exports = { "/api/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }`,
         });
 
         const { result, response } = await executeOnceAndFetch(harness, '/api/test');
@@ -92,7 +82,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -102,13 +92,10 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.js',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
-          'proxy.config.js': `export default { "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }`,
+          'proxy.config.js': `export default { "/api/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }`,
           'package.json': '{ "type": "module" }',
         });
 
@@ -117,7 +104,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -127,10 +114,9 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.cjs',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
+        const proxyAddress = proxyServer.address;
 
         await harness.writeFiles({
           'proxy.config.cjs': `module.exports = { "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }`,
@@ -141,7 +127,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -151,13 +137,10 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.mjs',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
-          'proxy.config.mjs': `export default { "/api/*": { "target": "http://127.0.0.1:${proxyAddress.port}" } }`,
+          'proxy.config.mjs': `export default { "/api/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }`,
         });
 
         const { result, response } = await executeOnceAndFetch(harness, '/api/test');
@@ -165,7 +148,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -175,13 +158,10 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         proxyConfig: 'proxy.config.json',
       });
 
-      const proxyServer = createProxyServer();
+      const proxyServer = await createProxyServer();
       try {
-        await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
-        const proxyAddress = proxyServer.address() as import('net').AddressInfo;
-
         await harness.writeFiles({
-          'proxy.config.json': `[ { "context": ["/api", "/abc"], "target": "http://127.0.0.1:${proxyAddress.port}" } ]`,
+          'proxy.config.json': `[ { "context": ["/api", "/abc"], "target": "http://127.0.0.1:${proxyServer.address.port}" } ]`,
         });
 
         const { result, response } = await executeOnceAndFetch(harness, '/api/test');
@@ -189,7 +169,7 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         expect(result?.success).toBeTrue();
         expect(await response?.text()).toContain('TEST_API_RETURN');
       } finally {
-        await new Promise<void>((resolve) => proxyServer.close(() => resolve()));
+        await proxyServer.close();
       }
     });
 
@@ -232,6 +212,29 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
         }),
       );
     });
+
+    it('supports negation of globs', async () => {
+      harness.useTarget('serve', {
+        ...BASE_OPTIONS,
+        proxyConfig: 'proxy.config.json',
+      });
+
+      const proxyServer = await createProxyServer();
+      try {
+        await harness.writeFiles({
+          'proxy.config.json': `
+              { "!something/**/*": { "target": "http://127.0.0.1:${proxyServer.address.port}" } }
+            `,
+        });
+
+        const { result, response } = await executeOnceAndFetch(harness, '/api/test');
+
+        expect(result?.success).toBeTrue();
+        expect(await response?.text()).toContain('TEST_API_RETURN');
+      } finally {
+        await proxyServer.close();
+      }
+    });
   });
 });
 
@@ -239,11 +242,9 @@ describeServeBuilder(executeDevServer, DEV_SERVER_BUILDER_INFO, (harness, setupT
  * Creates an HTTP Server used for proxy testing that provides a `/test` endpoint
  * that returns a 200 response with a body of `TEST_API_RETURN`. All other requests
  * will return a 404 response.
- *
- * @returns An HTTP Server instance.
  */
-function createProxyServer() {
-  return http.createServer((request, response) => {
+async function createProxyServer() {
+  const proxyServer = createServer((request, response) => {
     if (request.url?.endsWith('/test')) {
       response.writeHead(200);
       response.end('TEST_API_RETURN');
@@ -252,4 +253,11 @@ function createProxyServer() {
       response.end();
     }
   });
+
+  await new Promise<void>((resolve) => proxyServer.listen(0, '127.0.0.1', resolve));
+
+  return {
+    address: proxyServer.address() as import('net').AddressInfo,
+    close: () => new Promise<void>((resolve) => proxyServer.close(() => resolve())),
+  };
 }
diff --git a/packages/angular_devkit/build_angular/src/utils/load-proxy-config.ts b/packages/angular_devkit/build_angular/src/utils/load-proxy-config.ts
index 0bb8b36a95ea..76da35db34d9 100644
--- a/packages/angular_devkit/build_angular/src/utils/load-proxy-config.ts
+++ b/packages/angular_devkit/build_angular/src/utils/load-proxy-config.ts
@@ -11,7 +11,7 @@ import { existsSync } from 'node:fs';
 import { readFile } from 'node:fs/promises';
 import { extname, resolve } from 'node:path';
 import { pathToFileURL } from 'node:url';
-import { parse as parseGlob } from 'picomatch';
+import { makeRe as makeRegExpFromGlob } from 'picomatch';
 import { assertIsError } from './error';
 import { loadEsmModule } from './load-esm';
 
@@ -129,8 +129,8 @@ function normalizeProxyConfiguration(
   // TODO: Consider upstreaming glob support
   for (const key of Object.keys(normalizedProxy)) {
     if (isDynamicPattern(key)) {
-      const { output } = parseGlob(key);
-      normalizedProxy[`^${output}$`] = normalizedProxy[key];
+      const pattern = makeRegExpFromGlob(key).source;
+      normalizedProxy[pattern] = normalizedProxy[key];
       delete normalizedProxy[key];
     }
   }