--- old/src/java.base/share/classes/java/io/DeleteOnExitHook.java	2019-07-09 08:04:12.000000000 -0700
+++ new/src/java.base/share/classes/java/io/DeleteOnExitHook.java	2019-07-09 08:04:12.000000000 -0700
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2005, 2018, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2005, 2019, 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
@@ -64,6 +64,12 @@
         files.add(file);
     }
 
+    static synchronized void remove(String file) {
+        if(files != null) {
+            files.remove(file);
+        }
+    }
+
     static void runHooks() {
         LinkedHashSet<String> theFiles;
 
--- old/src/java.base/share/classes/java/io/File.java	2019-07-09 08:04:13.000000000 -0700
+++ new/src/java.base/share/classes/java/io/File.java	2019-07-09 08:04:12.000000000 -0700
@@ -164,6 +164,11 @@
     private final String path;
 
     /**
+     * Flag indicating whether this file path should be deleted on VM exit.
+     */
+    private boolean deleteOnExit;
+
+    /**
      * Enum type that indicates the status of a file path.
      */
     private static enum PathStatus { INVALID, CHECKED };
@@ -1021,7 +1026,11 @@
         if (isInvalid()) {
             throw new IOException("Invalid file path");
         }
-        return fs.createFileExclusively(path);
+        boolean result = fs.createFileExclusively(path);
+        if (deleteOnExit) {
+            deleteOnExit();
+        }
+        return result;
     }
 
     /**
@@ -1050,6 +1059,7 @@
         if (isInvalid()) {
             return false;
         }
+        DeleteOnExitHook.remove(path);
         return fs.delete(this);
     }
 
@@ -1089,6 +1099,7 @@
             return;
         }
         DeleteOnExitHook.add(path);
+        deleteOnExit = true;
     }
 
     /**
@@ -1325,7 +1336,11 @@
         if (isInvalid()) {
             return false;
         }
-        return fs.createDirectory(this);
+        boolean result = fs.createDirectory(this);
+        if (deleteOnExit) {
+            deleteOnExit();
+        }
+        return result;
     }
 
     /**
@@ -1363,8 +1378,12 @@
         }
 
         File parent = canonFile.getParentFile();
-        return (parent != null && (parent.mkdirs() || parent.exists()) &&
-                canonFile.mkdir());
+        boolean result = (parent != null &&
+            (parent.mkdirs() || parent.exists()) && canonFile.mkdir());
+        if (deleteOnExit) {
+            deleteOnExit();
+        }
+        return result;
     }
 
     /**