--- /dev/null	2019-10-13 13:09:59.932000000 +0000
+++ new/test/jdk/java/net/URLClassLoader/RemoveJar.java	2019-11-24 14:18:59.507706225 +0000
@@ -0,0 +1,164 @@
+/*
+ * Copyright (c) 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
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+/**
+ * @test
+ * @bug 8232854
+ *
+ * @run main/othervm RemoveJar true true testpkg.Test testpkg.Test testjar/
+ * @run main/othervm RemoveJar true true testpkg.Test testpkg.Missing testjar/
+ * @run main/othervm RemoveJar true true testpkg.Missing testpkg.Test testjar/
+ * @run main/othervm RemoveJar true true testpkg.Missing testpkg.Missing testjar/
+ *
+ * @run main/othervm RemoveJar true false testpkg.Test testpkg.Test testjar/
+ * @run main/othervm RemoveJar true false testpkg.Test testpkg.Missing testjar/
+ * @run main/othervm RemoveJar true false testpkg.Missing testpkg.Test testjar/
+ * @run main/othervm RemoveJar true false testpkg.Missing testpkg.Missing testjar/
+ *
+ * @run main/othervm RemoveJar false true testpkg.Test testpkg.Test testjar/
+ * @run main/othervm RemoveJar false true testpkg.Test testpkg.Missing testjar/
+ * @run main/othervm RemoveJar false true testpkg.Missing testpkg.Test testjar/
+ * @run main/othervm RemoveJar false true testpkg.Missing testpkg.Missing testjar/
+ *
+ * @run main/othervm RemoveJar false false testpkg.Test testpkg.Test testjar/
+ * @run main/othervm RemoveJar false false testpkg.Test testpkg.Missing testjar/
+ * @run main/othervm RemoveJar false false testpkg.Missing testpkg.Test testjar/
+ * @run main/othervm RemoveJar false false testpkg.Missing testpkg.Missing testjar/
+ *
+ * @run main/othervm RemoveJar true true testpkg.Test testpkg.Test badpath
+ *
+ * @summary URLClassLoader.close() doesn't close cached JAR file on Windows when load() fails
+ */
+
+import java.io.*;
+import java.net.*;
+import java.nio.file.*;
+import java.util.*;
+import java.util.stream.Stream;
+import java.util.zip.ZipException;
+import java.util.spi.ToolProvider;
+
+public class RemoveJar {
+    private final static String TEST_PKG = "testpkg";
+    private final static String JAR_DIR = "testjar/" + TEST_PKG;
+    private final static String FILE_NAME = "testjar.jar";
+    private final static ByteArrayOutputStream baos = new ByteArrayOutputStream();
+    private final static PrintStream out = new PrintStream(baos);
+    private final static ToolProvider JAR_TOOL = ToolProvider.findFirst("jar")
+        .orElseThrow(() ->
+            new RuntimeException("jar tool not found")
+        );
+
+    private static void buildJar() throws IOException {
+        // create dir
+        mkdir(JAR_DIR);
+        // create file
+        Path path = Paths.get(JAR_DIR);
+        String src = "package " + TEST_PKG + ";\n" +
+            "class Test {}\n";
+        Files.write(Paths.get(JAR_DIR + "/Test.java"), src.getBytes());
+        // compile class
+        compile(JAR_DIR + "/Test.java");
+        // package jar
+        jar("-cf testjar.jar " + JAR_DIR);
+    }
+
+    public static void main(String args[]) throws Exception {
+        buildJar();
+
+        URLClassLoader loader = null;
+        URL url = null;
+        Path path = Paths.get(FILE_NAME);
+
+        boolean useCacheFirst = Boolean.parseBoolean(args[0]);
+        boolean useCacheSecond = Boolean.parseBoolean(args[1]);
+        String firstClass = args[2];
+        String secondClass = args[3];
+        String subPath = args[4];
+
+        try {
+           String path_str = path.toUri().toURL().toString();
+           URLConnection.setDefaultUseCaches("jar", useCacheFirst);
+
+           url = new URL("jar", "", path_str + "!/" + subPath);
+           loader = new URLClassLoader(new URL[] { url });
+
+           loader.loadClass(firstClass);
+        } catch (Exception e) {
+           System.err.println("EXCEPTION: " + e);
+        }
+
+        try {
+            URLConnection.setDefaultUseCaches("jar", useCacheSecond);
+            loader.loadClass(secondClass);
+        } catch (Exception e) {
+           System.err.println("EXCEPTION: " + e);
+        } finally {
+           loader.close();
+           Files.delete(path);
+        }
+    }
+
+    private static Stream<Path> mkpath(String... args) {
+        return Arrays.stream(args).map(d -> Paths.get(".", d.split("/")));
+    }
+
+    private static void mkdir(String cmdline) {
+        System.out.println("mkdir -p " + cmdline);
+        mkpath(cmdline.split(" +")).forEach(p -> {
+            try {
+                Files.createDirectories(p);
+            } catch (IOException x) {
+                throw new UncheckedIOException(x);
+            }
+        });
+    }
+
+    private static void jar(String cmdline) throws IOException {
+        System.out.println("jar " + cmdline);
+        baos.reset();
+
+        // the run method catches IOExceptions, we need to expose them
+        ByteArrayOutputStream baes = new ByteArrayOutputStream();
+        PrintStream err = new PrintStream(baes);
+        PrintStream saveErr = System.err;
+        System.setErr(err);
+        int rc = JAR_TOOL.run(out, err, cmdline.split(" +"));
+        System.setErr(saveErr);
+        if (rc != 0) {
+            String s = baes.toString();
+            if (s.startsWith("java.util.zip.ZipException: duplicate entry: ")) {
+                throw new ZipException(s);
+            }
+            throw new IOException(s);
+        }
+    }
+
+    /* run javac <args> */
+    private static void compile(String... args) {
+        if (com.sun.tools.javac.Main.compile(args) != 0) {
+            throw new RuntimeException("javac failed: args=" + Arrays.toString(args));
+        }
+    }
+}
+