diff --git a/packages/angular/build/src/builders/application/tests/options/extract-licenses_spec.ts b/packages/angular/build/src/builders/application/tests/options/extract-licenses_spec.ts
index 402200a27f9d..2c495e703a7b 100644
--- a/packages/angular/build/src/builders/application/tests/options/extract-licenses_spec.ts
+++ b/packages/angular/build/src/builders/application/tests/options/extract-licenses_spec.ts
@@ -55,5 +55,96 @@ describeBuilder(buildApplication, APPLICATION_BUILDER_INFO, (harness) => {
       harness.expectFile('dist/3rdpartylicenses.txt').content.toContain('MIT');
       harness.expectFile('dist/browser/en-US/main.js').toExist();
     });
+
+    it(`should extract license from a package with a lowercase 'license' file`, async () => {
+      await harness.writeFile(
+        'node_modules/test-package-a/package.json',
+        JSON.stringify({
+          name: 'test-package-a',
+          version: '1.0.0',
+          main: 'index.js',
+          license: 'MIT',
+        }),
+      );
+      await harness.writeFile(
+        'node_modules/test-package-a/index.js',
+        'console.log("test-package-a");',
+      );
+      await harness.writeFile('node_modules/test-package-a/license', 'TEST_LOWERCASE_LICENSE_TEXT');
+      await harness.appendToFile('src/main.ts', "\nimport 'test-package-a';\n");
+
+      harness.useTarget('build', {
+        ...BASE_OPTIONS,
+        extractLicenses: true,
+      });
+
+      const { result } = await harness.executeOnce();
+      expect(result?.success).toBeTrue();
+      harness
+        .expectFile('dist/3rdpartylicenses.txt')
+        .content.toContain('TEST_LOWERCASE_LICENSE_TEXT');
+    });
+
+    it(`should extract license from a package with an alternative license file name (e.g., 'MIT-LICENCE.txt')`, async () => {
+      await harness.writeFile(
+        'node_modules/test-package-b/package.json',
+        JSON.stringify({
+          name: 'test-package-b',
+          version: '1.0.0',
+          main: 'index.js',
+          license: 'MIT',
+        }),
+      );
+      await harness.writeFile(
+        'node_modules/test-package-b/index.js',
+        'console.log("test-package-b");',
+      );
+      await harness.writeFile(
+        'node_modules/test-package-b/MIT-LICENCE.txt',
+        'TEST_ALTERNATIVE_LICENSE_TEXT',
+      );
+      await harness.appendToFile('src/main.ts', "\nimport 'test-package-b';\n");
+
+      harness.useTarget('build', {
+        ...BASE_OPTIONS,
+        extractLicenses: true,
+      });
+
+      const { result } = await harness.executeOnce();
+      expect(result?.success).toBeTrue();
+      harness
+        .expectFile('dist/3rdpartylicenses.txt')
+        .content.toContain('TEST_ALTERNATIVE_LICENSE_TEXT');
+    });
+
+    it(`should extract license from a package with a custom license file specified in package.json`, async () => {
+      await harness.writeFile(
+        'node_modules/test-package-c/package.json',
+        JSON.stringify({
+          name: 'test-package-c',
+          version: '1.0.0',
+          main: 'index.js',
+          license: 'SEE LICENSE IN custom-license.md',
+        }),
+      );
+      await harness.writeFile(
+        'node_modules/test-package-c/index.js',
+        'console.log("test-package-c");',
+      );
+      await harness.writeFile(
+        'node_modules/test-package-c/custom-license.md',
+        'TEST_CUSTOM_LICENSE_TEXT',
+      );
+      await harness.appendToFile('src/main.ts', "\nimport 'test-package-c';\n");
+
+      harness.useTarget('build', {
+        ...BASE_OPTIONS,
+        extractLicenses: true,
+      });
+
+      const { result } = await harness.executeOnce();
+      expect(result?.success).toBeTrue();
+      harness.expectFile('dist/3rdpartylicenses.txt').content.toContain('TEST_CUSTOM_LICENSE_TEXT');
+    });
   });
 });
diff --git a/packages/angular/build/src/tools/esbuild/license-extractor.ts b/packages/angular/build/src/tools/esbuild/license-extractor.ts
index 6629bbc387bf..890ebdd9826f 100644
--- a/packages/angular/build/src/tools/esbuild/license-extractor.ts
+++ b/packages/angular/build/src/tools/esbuild/license-extractor.ts
@@ -7,7 +7,7 @@
  */
 
 import type { Metafile } from 'esbuild';
-import { readFile } from 'node:fs/promises';
+import { readFile, readdir } from 'node:fs/promises';
 import path from 'node:path';
 
 /**
@@ -30,9 +30,9 @@ const NODE_MODULE_SEGMENT = 'node_modules';
 const CUSTOM_LICENSE_TEXT = 'SEE LICENSE IN ';
 
 /**
- * A list of commonly named license files found within packages.
+ * A regular expression for commonly named license files found within packages.
  */
-const LICENSE_FILES = ['LICENSE', 'LICENSE.txt', 'LICENSE.md'];
+const LICENSE_FILE_REGEXP = /^(?:mit-)?licen[cs]e(?:$|[-._])/i;
 
 /**
  * Header text that will be added to the top of the output license extraction file.
@@ -64,6 +64,7 @@ export async function extractLicenses(metafile: Metafile, rootDirectory: string)
   let extractedLicenseContent = `${EXTRACTION_FILE_HEADER}\n${EXTRACTION_FILE_SEPARATOR}`;
 
   const seenPaths = new Set<string>();
+  const seenPackageDirectories = new Set<string>();
   const seenPackages = new Set<string>();
 
   for (const entry of Object.values(metafile.outputs)) {
@@ -110,6 +111,11 @@ export async function extractLicenses(metafile: Metafile, rootDirectory: string)
         : nameOrScope;
       const packageDirectory = path.join(baseDirectory, packageName);
 
+      if (seenPackageDirectories.has(packageDirectory)) {
+        continue;
+      }
+      seenPackageDirectories.add(packageDirectory);
+
       // Load the package's metadata to find the package's name, version, and license type
       const packageJsonPath = path.join(packageDirectory, 'package.json');
       let packageJson;
@@ -136,12 +142,12 @@ export async function extractLicenses(metafile: Metafile, rootDirectory: string)
       let licenseText = '';
       if (
         typeof packageJson.license === 'string' &&
-        packageJson.license.toLowerCase().startsWith(CUSTOM_LICENSE_TEXT)
+        packageJson.license.toUpperCase().startsWith(CUSTOM_LICENSE_TEXT)
       ) {
         // Attempt to load the package's custom license
         let customLicensePath;
         const customLicenseFile = path.normalize(
-          packageJson.license.slice(CUSTOM_LICENSE_TEXT.length + 1).trim(),
+          packageJson.license.slice(CUSTOM_LICENSE_TEXT.length).trim(),
         );
         if (customLicenseFile.startsWith('..') || path.isAbsolute(customLicenseFile)) {
           // Path is attempting to access files outside of the package
@@ -150,17 +156,20 @@ export async function extractLicenses(metafile: Metafile, rootDirectory: string)
           customLicensePath = path.join(packageDirectory, customLicenseFile);
           try {
             licenseText = await readFile(customLicensePath, 'utf-8');
-            break;
           } catch {}
         }
       } else {
         // Search for a license file within the root of the package
-        for (const potentialLicense of LICENSE_FILES) {
-          const packageLicensePath = path.join(packageDirectory, potentialLicense);
-          try {
-            licenseText = await readFile(packageLicensePath, 'utf-8');
-            break;
-          } catch {}
+        const entries = await readdir(packageDirectory, { withFileTypes: true }).catch(() => []);
+
+        for (const entry of entries) {
+          if ((entry.isFile() || entry.isSymbolicLink()) && LICENSE_FILE_REGEXP.test(entry.name)) {
+            const packageLicensePath = path.join(packageDirectory, entry.name);
+            try {
+              licenseText = await readFile(packageLicensePath, 'utf-8');
+              break;
+            } catch {}
+          }
         }
       }