diff --git a/test/jdk/sun/net/www/protocol/http/NTLMHeadTest.java b/test/jdk/sun/net/www/protocol/http/NTLMHeadTest.java
index 52174ab2f55..2cbbf5f6534 100644
--- a/test/jdk/sun/net/www/protocol/http/NTLMHeadTest.java
+++ b/test/jdk/sun/net/www/protocol/http/NTLMHeadTest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2021, 2022, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2021, 2026, Oracle and/or its affiliates. All rights reserved.
  * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
  *
  * This code is free software; you can redistribute it and/or modify it
@@ -22,8 +22,9 @@
  */
 
 /*
- * @test
+ * @test id=default
  * @bug 8270290
+ * @requires os.family != "windows"
  * @library /test/lib
  * @run main/othervm NTLMHeadTest SERVER
  * @run main/othervm NTLMHeadTest PROXY
@@ -48,6 +49,17 @@
  *      include the body.
  */
 
+/*
+ * @test id=windows
+ * @bug 8270290
+ * @comment Only run on specific Windows OS versions because NTLMv1 is no longer supported starting Windows 11 and Windows Server 2025
+ * @requires os.family == "windows" & (os.name == "Windows 10" | os.name == "Windows Server 2016" | os.name == "Windows Server 2019" | os.name == "Windows Server 2022")
+ * @library /test/lib
+ * @run main/othervm NTLMHeadTest SERVER
+ * @run main/othervm NTLMHeadTest PROXY
+ * @run main/othervm NTLMHeadTest TUNNEL
+ */
+
 import java.net.*;
 import java.io.*;
 import java.util.*;
diff --git a/test/jdk/sun/net/www/protocol/http/TestTransparentNTLM.java b/test/jdk/sun/net/www/protocol/http/TestTransparentNTLM.java
index 1c2262ba8e2..7a8082a4012 100644
--- a/test/jdk/sun/net/www/protocol/http/TestTransparentNTLM.java
+++ b/test/jdk/sun/net/www/protocol/http/TestTransparentNTLM.java
@@ -26,7 +26,8 @@
  * @bug 8225425
  * @summary Verifies that transparent NTLM (on Windows) is not used by default,
  *          and is used only when the relevant property is set.
- * @requires os.family == "windows"
+ * @comment Only run on specific Windows OS versions because NTLMv1 is no longer supported starting Windows 11 and Windows Server 2025
+ * @requires os.family == "windows" & (os.name == "Windows 10" | os.name == "Windows Server 2016" | os.name == "Windows Server 2019" | os.name == "Windows Server 2022")
  * @library /test/lib
  * @run junit/othervm
  *      -Dtest.auth.succeed=false