diff --git a/packages/flutter_tools/lib/src/build_system/targets/macos.dart b/packages/flutter_tools/lib/src/build_system/targets/macos.dart
index 8981bb48a02..366268d59f0 100644
--- a/packages/flutter_tools/lib/src/build_system/targets/macos.dart
+++ b/packages/flutter_tools/lib/src/build_system/targets/macos.dart
@@ -62,6 +62,8 @@ abstract class UnpackMacOS extends Target {
       basePath,
       environment.outputDir.path,
     ]);
+
+    _removeDenylistedFiles(environment.outputDir);
     if (result.exitCode != 0) {
       throw Exception(
         'Failed to copy framework (exit ${result.exitCode}:\n'
@@ -81,6 +83,19 @@ abstract class UnpackMacOS extends Target {
     _thinFramework(environment, frameworkBinaryPath);
   }
 
+  static const List<String> _copyDenylist = <String>['entitlements.txt', 'without_entitlements.txt'];
+
+  void _removeDenylistedFiles(Directory directory) {
+    for (final FileSystemEntity entity in directory.listSync(recursive: true)) {
+      if (entity is! File) {
+        continue;
+      }
+      if (_copyDenylist.contains(entity.basename)) {
+        entity.deleteSync();
+      }
+    }
+  }
+
   void _thinFramework(Environment environment, String frameworkBinaryPath) {
     final String archs = environment.defines[kDarwinArchs] ?? 'x86_64 arm64';
     final List<String> archList = archs.split(' ').toList();
diff --git a/packages/flutter_tools/test/general.shard/build_system/targets/macos_test.dart b/packages/flutter_tools/test/general.shard/build_system/targets/macos_test.dart
index 176b76b9ad1..2d705301e0f 100644
--- a/packages/flutter_tools/test/general.shard/build_system/targets/macos_test.dart
+++ b/packages/flutter_tools/test/general.shard/build_system/targets/macos_test.dart
@@ -106,6 +106,51 @@ void main() {
     ProcessManager: () => processManager,
   });
 
+  testUsingContext('deletes entitlements.txt and without_entitlements.txt files after copying', () async {
+    binary.createSync(recursive: true);
+    final File entitlements = environment.outputDir.childFile('entitlements.txt');
+    final File withoutEntitlements = environment.outputDir.childFile('without_entitlements.txt');
+    final File nestedEntitlements = environment
+        .outputDir
+        .childDirectory('first_level')
+        .childDirectory('second_level')
+        .childFile('entitlements.txt')
+        ..createSync(recursive: true);
+
+    processManager.addCommands(<FakeCommand>[
+      FakeCommand(
+        command: <String>[
+          'rsync',
+          '-av',
+          '--delete',
+          '--filter',
+          '- .DS_Store/',
+          // source
+          'Artifact.flutterMacOSFramework.debug',
+          // destination
+          environment.outputDir.path,
+        ],
+        onRun: () {
+          entitlements.writeAsStringSync('foo');
+          withoutEntitlements.writeAsStringSync('bar');
+          nestedEntitlements.writeAsStringSync('somefile.bin');
+        },
+      ),
+      lipoInfoNonFatCommand,
+      lipoVerifyX86_64Command,
+    ]);
+
+    await const DebugUnpackMacOS().build(environment);
+    expect(entitlements.existsSync(), isFalse);
+    expect(withoutEntitlements.existsSync(), isFalse);
+    expect(nestedEntitlements.existsSync(), isFalse);
+
+    expect(processManager, hasNoRemainingExpectations);
+  }, overrides: <Type, Generator>{
+    FileSystem: () => fileSystem,
+    ProcessManager: () => processManager,
+  });
+
   testUsingContext('thinning fails when framework missing', () async {
     processManager.addCommand(copyFrameworkCommand);
     await expectLater(