diff --git a/src/res/node.exe.extra.manifest b/src/res/node.exe.extra.manifest
index e2e9f175473305..8be0a7e830153e 100644
--- a/src/res/node.exe.extra.manifest
+++ b/src/res/node.exe.extra.manifest
@@ -14,4 +14,9 @@
       <supportedOS Id="{e2011457-1546-43c5-a5fe-008deee3d3f0}"/>
   </application>
   </compatibility>
+  <application xmlns="urn:schemas-microsoft-com:asm.v3">
+    <windowsSettings xmlns:ws2="http://schemas.microsoft.com/SMI/2016/WindowsSettings">
+      <ws2:longPathAware>true</ws2:longPathAware>
+    </windowsSettings>
+  </application>
 </assembly>
diff --git a/test/parallel/test-fs-long-path.js b/test/parallel/test-fs-long-path.js
index 1cb66fa6046152..3f808496ae53f2 100644
--- a/test/parallel/test-fs-long-path.js
+++ b/test/parallel/test-fs-long-path.js
@@ -43,4 +43,7 @@ console.log({
 
 fs.writeFile(fullPath, 'ok', common.mustSucceed(() => {
   fs.stat(fullPath, common.mustSucceed());
+
+  // Tests https://github.com/nodejs/node/issues/39721
+  fs.realpath.native(fullPath, common.mustSucceed());
 }));