ADDITIONAL SYSTEM INFORMATION :
Macbook Pro 15-inch 2016
Mac OS X High Sierra 10.13.5
OpenJDK jdk-10.0.1.jdk & jdk-11.jdk

A DESCRIPTION OF THE PROBLEM :
I have observed that when building a Jar using JarOutputStream, when adding a JarEntry if I call JarEntry.setLastModifiedTime prior to calling setTime, the Jar is built incorrectly and reading it using java.util.jar.JarFile will throw an exception.

java.util.zip.ZipException: invalid CEN header (bad header size)

Expected Results: Regardless of order, or calls to these methods should produce a valid Jar file or exception while writing the Jar file to indicate the error. 




REGRESSION : Last worked in version 8u171

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
1. Open a JarOutputStream
2. Create a single JarEntry
3. setCreationTime
4. setLastAccessTime
5. setLastModifiedTime
6. setTime
7. JarOutputStream.putNextEntry

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
Expect the Jar to be built correctly or for the JarOutputStream to fail if it is unable to be built correctly. 

This previously worked on Oracle JRE jdk1.8.0_171 and earlier.
ACTUAL -
The JarOutputStream does not fail, but the jar is not built correctly, and then reading the jar using java.util.jar.JarFile will throw java.util.zip.ZipException: invalid CEN header (bad header size).

I can recreate these results on Open JDK 10.0.1 and 11.

---------- BEGIN SOURCE ----------
import java.io.File;
import java.io.IOException;
import java.nio.file.Files;
import java.nio.file.Path;
import java.nio.file.Paths;
import java.nio.file.attribute.FileTime;
import java.util.function.Consumer;
import java.util.jar.JarEntry;
import java.util.jar.JarFile;
import java.util.jar.JarOutputStream;
import java.util.jar.Manifest;
import java.util.zip.ZipException;

/**
 * @author Daniel DeGroff
 */
public class JarOutputStreamTest {

  public static void main(String[] args) throws IOException {

    // Create a test file to include in the jar.
    Files.deleteIfExists(Paths.get("./foo"));
    Path file = Files.createFile(Paths.get("./foo"));

    FileTime creationTime = (FileTime) Files.getAttribute(file, "creationTime");
    FileTime lastAccessTime = (FileTime) Files.getAttribute(file, "lastAccessTime");
    FileTime lastModifiedTime = Files.getLastModifiedTime(file);

    File jarFile = new File("testcase");
    jarFile.deleteOnExit();

    // 1. Passes, order is Ok.
    runTestCase(jarFile, file, entry -> {
      entry.setCreationTime(creationTime);
      entry.setLastAccessTime(lastAccessTime);

      // Calling setTime prior to setLastModifiedTime is Ok.
      entry.setTime(lastModifiedTime.toMillis());
      entry.setLastModifiedTime(lastModifiedTime);
    });

    // 2. Passes, omit the call to setTime
    runTestCase(jarFile, file, entry -> {
      entry.setCreationTime(creationTime);
      entry.setLastAccessTime(lastAccessTime);

      // Omitting the call to setTime is Ok.
      entry.setLastModifiedTime(lastModifiedTime);
    });

    // 3. Passes, omit setCreationTime and setLastAccessTime then order does not matter
    runTestCase(jarFile, file, entry -> {
      // Calling these two in either order is ok when we don't call setCreationTime and setLastAccessTime
      entry.setTime(lastModifiedTime.toMillis());
      entry.setLastModifiedTime(lastModifiedTime);
    });

    // 4. Passes, omit setCreationTime and setLastAccessTime then order does not matter
    runTestCase(jarFile, file, entry -> {
      // Calling these two in either order is ok when we don't call setCreationTime and setLastAccessTime
      entry.setLastModifiedTime(lastModifiedTime);
      entry.setTime(lastModifiedTime.toMillis());
    });

    // 5. Fails
    runTestCase(jarFile, file, entry -> {
      entry.setCreationTime(creationTime);
      entry.setLastAccessTime(lastAccessTime);

      // Calling setLastModifiedTime prior to setTime when also calling setCreationTime and setLastAccessTime fails.
      entry.setLastModifiedTime(lastModifiedTime);
      entry.setTime(lastModifiedTime.toMillis());
    });
  }


  private static void runTestCase(File jarFile, Path file, Consumer<JarEntry> consumer) throws IOException {
    try (JarOutputStream jos = new JarOutputStream(Files.newOutputStream(jarFile.toPath()), new Manifest())) {
      JarEntry entry = new JarEntry(file.toString());
      consumer.accept(entry);
      entry.setSize((Long) Files.getAttribute(file, "size"));
      jos.putNextEntry(entry);
      jos.flush();
      jos.closeEntry();
    }

    try {
      new JarFile(jarFile);
      System.out.println("Success!");
    } catch (ZipException e) {
      // Throws java.util.zip.ZipException: invalid CEN header (bad header size)
      System.out.println("Fail. " + e.getClass().getCanonicalName() + ": " + e.getMessage());
    }
  }
}

---------- END SOURCE ----------

CUSTOMER SUBMITTED WORKAROUND :
Workaround 1:

Call JarEntry.setTime before JarEntry.setLastModifiedTime

Workaround 2:

Leave setLastModifiedTime before setTime but omit setCreationTime and setLastAccessTime

Workaround 3:

Do not call setTime, instead only call setCreationTime, setLastAccessTime, and setLastModifiedTime

 

FREQUENCY : always