[java] file.delete() returns false even though file.exists(), file.canRead(), file.canWrite(), file.canExecute() all return true

Another corner case that this could happen: if you read/write a JAR file through a URL and later try to delete the same file within the same JVM session.

File f = new File("/tmp/foo.jar");
URL j = f.toURI().toURL();

URL u = new URL("jar:" + j + "!/META-INF/MANIFEST.MF");
URLConnection c = u.openConnection();

// open a Jar entry in auto-closing manner
try (InputStream i = c.getInputStream()) {

    // just read some stuff; for demonstration purposes only
    byte[] first16 = new byte[16];
    i.read(first16);
    System.out.println(new String(first16));
}

// ...

// i is now closed, so we should be good to delete the jar; but...
System.out.println(f.delete());     // says false!

Reason is that the internal JAR file handling logic of Java, tends to cache JarFile entries:

// inner class of `JarURLConnection` that wraps the actual stream returned by `getInputStream()`

class JarURLInputStream extends FilterInputStream {
    JarURLInputStream(InputStream var2) {
        super(var2);
    }

    public void close() throws IOException {
        try {
            super.close();
        } finally {

            // if `getUseCaches()` is set, `jarFile` won't get closed!

            if (!JarURLConnection.this.getUseCaches()) {
                JarURLConnection.this.jarFile.close();
            }
        }
    }
}

And each JarFile (rather, the underlying ZipFile structure) would hold a handle to the file, right from the time of construction up until close() is invoked:

public ZipFile(File file, int mode, Charset charset) throws IOException {
    // ...

    jzfile = open(name, mode, file.lastModified(), usemmap);

    // ...
}

// ...

private static native long open(String name, int mode, long lastModified,
                                boolean usemmap) throws IOException;

There's a good explanation on this NetBeans issue.

Apparently there are two ways to "fix" this:

• You can disable the JAR file caching - for the current URLConnection, or for all future URLConnections (globally) in the current JVM session:

  URL u = new URL("jar:" + j + "!/META-INF/MANIFEST.MF");
  URLConnection c = u.openConnection();
  
  // for only c
  c.setUseCaches(false);
  
  // globally; for some reason this method is not static,
  // so we still need to access it through a URLConnection instance :(
  c.setDefaultUseCaches(false);
  

• [HACK WARNING!] You can manually purge the JarFile from the cache when you are done with it. The cache manager sun.net.www.protocol.jar.JarFileFactory is package-private, but some reflection magic can get the job done for you:

  class JarBridge {
  
      static void closeJar(URL url) throws Exception {
  
          // JarFileFactory jarFactory = JarFileFactory.getInstance();
          Class<?> jarFactoryClazz = Class.forName("sun.net.www.protocol.jar.JarFileFactory");
          Method getInstance = jarFactoryClazz.getMethod("getInstance");
          getInstance.setAccessible(true);
          Object jarFactory = getInstance.invoke(jarFactoryClazz);
  
          // JarFile jarFile = jarFactory.get(url);
          Method get = jarFactoryClazz.getMethod("get", URL.class);
          get.setAccessible(true);
          Object jarFile = get.invoke(jarFactory, url);
  
          // jarFactory.close(jarFile);
          Method close = jarFactoryClazz.getMethod("close", JarFile.class);
          close.setAccessible(true);
          //noinspection JavaReflectionInvocation
          close.invoke(jarFactory, jarFile);
  
          // jarFile.close();
          ((JarFile) jarFile).close();
      }
  }
  
  // and in your code:
  
  // i is now closed, so we should be good to delete the jar
  JarBridge.closeJar(j);
  System.out.println(f.delete());     // says true, phew.
  

Please note: All this is based on Java 8 codebase (1.8.0_144); they may not work with other / later versions.