Note: The underlying cause is in core libs (JDK-8366736). If that cannot be easily fixed, we might try to implement a work-around in this bug (JDK-8366731).
=========
With a program like this:

import java.io.*;
public class PrintWriterTest {
    public static void main(String args[]) throws Throwable {
        System.out.println("Before");

        try (var log = new PrintWriter(System.err);
             var ref = new PrintWriter(System.out)) {
          System.err.println("Middle with System.err");
          for (int i = 0; i < 1; i++) {
            log.println("Middle with log");
          }
        }

        System.out.println("Done");
    }
}


$ java.exe -cp app.jar -XX:AOTCacheOutput=app.aot PrintWriterTest
Before
Middle with System.err

Program finishes, but not that "Done" is not printed, because System.out has been closed

$ java.exe -cp app.jar -XX:AOTCacheOutput=app.aot -Xlog:aot PrintWriterTest
[0.003s][info][aot] Selected AOTMode=record because AOTCacheOutput is specified
[0.020s][info][aot] Core region alignment: 65536
Before
Middle with System.err

Program gets stuck here, because child process cannot write its output and gets stuck, causing the process to wait here forever.

"main" #3 [43936] prio=5 os_prio=0 cpu=546.88ms elapsed=21.23s tid=0x000001fd23fbb550 nid=43936 runnable [0x00000061f29fd000]
   java.lang.Thread.State: RUNNABLE
Thread: 0x000001fd23fbb550 [0xaba0] State: _at_safepoint _at_poll_safepoint 0
   JavaThread state: _thread_in_native
        at java.lang.ProcessImpl.waitForInterruptibly(java.base@26-internal/Native Method)
        at java.lang.ProcessImpl.waitFor(java.base@26-internal/ProcessImpl.java:555)
        at jdk.internal.misc.CDS$ProcessLauncher.execWithJavaToolOptions(java.base@26-internal/CDS.java:549)
        at java.lang.Shutdown.halt0(java.base@26-internal/Native Method)
        at java.lang.Shutdown.halt(java.base@26-internal/Shutdown.java:149)
        - locked <0x00000006408e2758> (a java.lang.Shutdown$Lock)
        at java.lang.Shutdown.exit(java.base@26-internal/Shutdown.java:168)
        - locked <0x00000006408e2538> (a java.lang.Class for java.lang.Shutdown)
        at java.lang.Runtime.exit(java.base@26-internal/Runtime.java:177)
        at java.lang.System.exit(java.base@26-internal/System.java:1540)
        at javasoft.sqe.javatest.Status.exit(Status.java:235)
        at javasoft.sqe.tests.api.java.lang.ThreadGroup.toString.toString0101.toString0101.main(toString0101.java:40)


=============
Impact:
This happens more often on Windows, but it could affect other platforms as well, if the amount of logging exceeds the OS's buffer for child process output.

=============
Work around:
[1] Do not close System.err/out in your program if you want to use -XX:AOTCacheOutput.

or

[2] Use the two step AOT workflow -XX:AOTMode=record, and then AOTMode=create , in separate processes.