diff --git a/changelog.html b/changelog.html
index e33098e255..339ce25cf8 100644
--- a/changelog.html
+++ b/changelog.html
@@ -55,6 +55,9 @@ Upcoming changes</a>
 <!-- Record your changes in the trunk here. -->
 <div id="trunk" style="display:none"><!--=TRUNK-BEGIN=-->
 <ul class=image>
+  <li class=bug>
+    Fixed a bug in the auto-overwrite of bundled plugins on Windows.
+    (<a href="https://issues.jenkins-ci.org/browse/JENKINS-12514">issue 12514</a>)
   <li class=bug>
     Fixed a temporary memory spike when dealing with rapidly growing large console output and interactive monitoring.
   <li class=bug>
diff --git a/core/src/main/java/hudson/PluginManager.java b/core/src/main/java/hudson/PluginManager.java
index 35e3c8ba2e..75be36bb73 100644
--- a/core/src/main/java/hudson/PluginManager.java
+++ b/core/src/main/java/hudson/PluginManager.java
@@ -414,12 +414,9 @@ public abstract class PluginManager extends AbstractModelObject {
         File file = new File(rootDir, fileName);
         File pinFile = new File(rootDir, fileName+".pinned");
 
-        {// normalization first
-            File legacyFile = new File(rootDir,legacyName);
-            if (legacyFile.exists())    legacyFile.renameTo(file);
-            File legacyPinFile = new File(rootDir,legacyName+".pinned");
-            if (legacyPinFile.exists())    legacyPinFile.renameTo(pinFile);
-        }
+        // normalization first, if the old file exists.
+        rename(new File(rootDir,legacyName),file);
+        rename(new File(rootDir,legacyName+".pinned"),pinFile);
         
         // update file if:
         //  - no file exists today
@@ -434,6 +431,20 @@ public abstract class PluginManager extends AbstractModelObject {
         }
     }
 
+    /**
+     * Rename a legacy file to a new name, with care to Windows where {@link File#renameTo(File)}
+     * doesn't work if the destination already exists.
+     */
+    private void rename(File legacyFile, File newFile) throws IOException {
+        if (!legacyFile.exists())   return;
+        if (newFile.exists()) {
+            Util.deleteFile(newFile);
+        }
+        if (!legacyFile.renameTo(newFile)) {
+            LOGGER.warning("Failed to rename " + legacyFile + " to " + newFile);
+        }
+    }
+
     /**
      * Creates a hudson.PluginStrategy, looking at the corresponding system property. 
      */