diff --git a/test/src/main/java/org/jvnet/hudson/test/HudsonTestCase.java b/test/src/main/java/org/jvnet/hudson/test/HudsonTestCase.java
index 42fe5eb83d7a78651e47b1bde8d4c5dc0c6028a2..066ce52cea488a2dbc58ee8ed70bf54183759ffc 100644
--- a/test/src/main/java/org/jvnet/hudson/test/HudsonTestCase.java
+++ b/test/src/main/java/org/jvnet/hudson/test/HudsonTestCase.java
@@ -101,6 +101,7 @@ import java.net.MalformedURLException;
 import java.net.URISyntaxException;
 import java.net.URL;
 import java.net.URLClassLoader;
+import java.net.URLConnection;
 import java.nio.charset.Charset;
 import java.util.ArrayList;
 import java.util.Arrays;
@@ -276,6 +277,8 @@ public abstract class HudsonTestCase extends TestCase implements RootAction {
      */
     protected File explodedWarDir;
 
+    private boolean origDefaultUseCache = true;
+
     protected HudsonTestCase(String name) {
         super(name);
     }
@@ -298,6 +301,18 @@ public abstract class HudsonTestCase extends TestCase implements RootAction {
 
     @Override
     protected void  setUp() throws Exception {
+        if(Functions.isWindows()) {
+            // JENKINS-4409.
+            // URLConnection caches handles to jar files by default,
+            // and it prevents delete temporary directories on Windows.
+            // Disables caching here.
+            // Though defaultUseCache is a static field,
+            // its setter and getter are provided as instance methods.
+            URLConnection aConnection = new File(".").toURI().toURL().openConnection();
+            origDefaultUseCache = aConnection.getDefaultUseCaches();
+            aConnection.setDefaultUseCaches(false);
+        }
+        
         env.pin();
         recipe();
         for (Runner r : recipes) {
@@ -425,6 +440,12 @@ public abstract class HudsonTestCase extends TestCase implements RootAction {
             // at some later point, leading to possible file descriptor overflow. So encourage GC now.
             // see http://bugs.sun.com/view_bug.do?bug_id=4950148
             System.gc();
+            
+            // restore defaultUseCache
+            if(Functions.isWindows()) {
+                URLConnection aConnection = new File(".").toURI().toURL().openConnection();
+                aConnection.setDefaultUseCaches(origDefaultUseCache);
+            }
         }
     }
 
diff --git a/test/src/main/java/org/jvnet/hudson/test/JenkinsRule.java b/test/src/main/java/org/jvnet/hudson/test/JenkinsRule.java
index 3c2eb131500f0dde0882c19a544a4304c749901e..b9707a2f63d7a145db3d2b70725efc239aa56e17 100644
--- a/test/src/main/java/org/jvnet/hudson/test/JenkinsRule.java
+++ b/test/src/main/java/org/jvnet/hudson/test/JenkinsRule.java
@@ -128,6 +128,7 @@ import java.net.SocketTimeoutException;
 import java.net.URISyntaxException;
 import java.net.URL;
 import java.net.URLClassLoader;
+import java.net.URLConnection;
 import java.nio.charset.Charset;
 import java.util.ArrayList;
 import java.util.Arrays;
@@ -303,6 +304,8 @@ public class JenkinsRule implements TestRule, MethodRule, RootAction {
 
     public JenkinsComputerConnectorTester computerConnectorTester = new JenkinsComputerConnectorTester(this);
 
+    private boolean origDefaultUseCache = true;
+
     public Jenkins getInstance() {
         return jenkins;
     }
@@ -312,6 +315,18 @@ public class JenkinsRule implements TestRule, MethodRule, RootAction {
      * @throws Throwable if setup fails (which will disable {@code after}
      */
     public void before() throws Throwable {
+        if(Functions.isWindows()) {
+            // JENKINS-4409.
+            // URLConnection caches handles to jar files by default,
+            // and it prevents delete temporary directories on Windows.
+            // Disables caching here.
+            // Though defaultUseCache is a static field,
+            // its setter and getter are provided as instance methods.
+            URLConnection aConnection = new File(".").toURI().toURL().openConnection();
+            origDefaultUseCache = aConnection.getDefaultUseCaches();
+            aConnection.setDefaultUseCaches(false);
+        }
+        
         // Not ideal (https://github.com/junit-team/junit/issues/116) but basically works.
         if (Boolean.getBoolean("ignore.random.failures")) {
             RandomlyFails rf = testDescription.getAnnotation(RandomlyFails.class);
@@ -458,6 +473,12 @@ public class JenkinsRule implements TestRule, MethodRule, RootAction {
             // see http://bugs.sun.com/view_bug.do?bug_id=4950148
             // TODO use URLClassLoader.close() in Java 7
             System.gc();
+            
+            // restore defaultUseCache
+            if(Functions.isWindows()) {
+                URLConnection aConnection = new File(".").toURI().toURL().openConnection();
+                aConnection.setDefaultUseCaches(origDefaultUseCache);
+            }
         }
     }