--- old/src/solaris/classes/java/lang/UNIXProcess.java	2019-08-29 13:05:50.000000000 -0700
+++ new/src/solaris/classes/java/lang/UNIXProcess.java	2019-08-29 13:05:49.000000000 -0700
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 1995, 2014, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 1995, 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
@@ -408,8 +408,7 @@
         long deadline = System.nanoTime() + remainingNanos;
 
         do {
-            // Round up to next millisecond
-            wait(TimeUnit.NANOSECONDS.toMillis(remainingNanos + 999_999L));
+            TimeUnit.NANOSECONDS.timedWait(this, remainingNanos);
             if (hasExited) {
                 return true;
             }
--- old/src/windows/classes/java/lang/ProcessImpl.java	2019-08-29 13:05:52.000000000 -0700
+++ new/src/windows/classes/java/lang/ProcessImpl.java	2019-08-29 13:05:51.000000000 -0700
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 1995, 2013, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 1995, 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
@@ -462,11 +462,15 @@
         if (timeout <= 0) return false;
 
         long remainingNanos  = unit.toNanos(timeout);
-        long deadline = System.nanoTime() + remainingNanos ;
+        long deadline = System.nanoTime() + remainingNanos;
 
         do {
             // Round up to next millisecond
             long msTimeout = TimeUnit.NANOSECONDS.toMillis(remainingNanos + 999_999L);
+            if (msTimeout < 0) {
+                // if wraps around then wait a long while
+                msTimeout = Integer.MAX_VALUE;
+            }
             waitForTimeoutInterruptibly(handle, msTimeout);
             if (Thread.interrupted())
                 throw new InterruptedException();
@@ -480,7 +484,7 @@
     }
 
     private static native void waitForTimeoutInterruptibly(
-        long handle, long timeout);
+        long handle, long timeoutMillis);
 
     public void destroy() { terminateProcess(handle); }
 
--- old/src/windows/native/java/lang/ProcessImpl_md.c	2019-08-29 13:05:54.000000000 -0700
+++ new/src/windows/native/java/lang/ProcessImpl_md.c	2019-08-29 13:05:53.000000000 -0700
@@ -421,10 +421,10 @@
 Java_java_lang_ProcessImpl_waitForTimeoutInterruptibly(JNIEnv *env,
                                                        jclass ignored,
                                                        jlong handle,
-                                                       jlong timeout)
+                                                       jlong timeoutMillis)
 {
     HANDLE events[2];
-    DWORD dwTimeout = (DWORD)timeout;
+    DWORD dwTimeout = (DWORD)timeoutMillis;
     DWORD result;
     events[0] = (HANDLE) handle;
     events[1] = JVM_GetThreadInterruptEvent();
--- old/test/java/lang/ProcessBuilder/Basic.java	2019-08-29 13:05:55.000000000 -0700
+++ new/test/java/lang/ProcessBuilder/Basic.java	2019-08-29 13:05:55.000000000 -0700
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2003, 2013, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2003, 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
@@ -61,6 +61,15 @@
     /* used for AIX only */
     static final String libpath = System.getenv("LIBPATH");
 
+    /**
+     * Returns the number of milliseconds since time given by
+     * startNanoTime, which must have been previously returned from a
+     * call to {@link System.nanoTime()}.
+     */
+    private static long millisElapsedSince(long startNanoTime) {
+        return TimeUnit.NANOSECONDS.toMillis(System.nanoTime() - startNanoTime);
+    }
+
     private static String commandOutput(Reader r) throws Throwable {
         StringBuilder sb = new StringBuilder();
         int c;
@@ -2294,40 +2303,65 @@
 
         //----------------------------------------------------------------
         // Check that Process.waitFor(timeout, TimeUnit.MILLISECONDS)
-        // interrupt works as expected.
+        // interrupt works as expected, if interrupted while waiting.
         //----------------------------------------------------------------
         try {
             List<String> childArgs = new ArrayList<String>(javaChildArgs);
             childArgs.add("sleep");
             final Process p = new ProcessBuilder(childArgs).start();
             final long start = System.nanoTime();
-            final CountDownLatch ready = new CountDownLatch(1);
-            final CountDownLatch done = new CountDownLatch(1);
+            final CountDownLatch aboutToWaitFor = new CountDownLatch(1);
 
             final Thread thread = new Thread() {
                 public void run() {
                     try {
-                        final boolean result;
-                        try {
-                            ready.countDown();
-                            result = p.waitFor(30000, TimeUnit.MILLISECONDS);
-                        } catch (InterruptedException e) {
-                            return;
-                        }
+                        aboutToWaitFor.countDown();
+                        Thread.currentThread().interrupt();
+                        boolean result = p.waitFor(30L * 1000L, TimeUnit.MILLISECONDS);
                         fail("waitFor() wasn't interrupted, its return value was: " + result);
-                    } catch (Throwable t) {
-                        unexpected(t);
-                    } finally {
-                        done.countDown();
-                    }
+                    } catch (InterruptedException success) {
+                    } catch (Throwable t) { unexpected(t); }
+                }
+            };
+
+            thread.start();
+            aboutToWaitFor.await();
+            thread.interrupt();
+            thread.join(10L * 1000L);
+            check(millisElapsedSince(start) < 10L * 1000L);
+            check(!thread.isAlive());
+            p.destroy();
+        } catch (Throwable t) { unexpected(t); }
+
+        //----------------------------------------------------------------
+        // Check that Process.waitFor(Long.MAX_VALUE, TimeUnit.MILLISECONDS)
+        // interrupt works as expected, if interrupted while waiting.
+        //----------------------------------------------------------------
+        try {
+            List<String> childArgs = new ArrayList<String>(javaChildArgs);
+            childArgs.add("sleep");
+            final Process p = new ProcessBuilder(childArgs).start();
+            final long start = System.nanoTime();
+            final CountDownLatch aboutToWaitFor = new CountDownLatch(1);
+
+            final Thread thread = new Thread() {
+                public void run() {
+                    try {
+                        aboutToWaitFor.countDown();
+                        Thread.currentThread().interrupt();
+                        boolean result = p.waitFor(Long.MAX_VALUE, TimeUnit.MILLISECONDS);
+                        fail("waitFor() wasn't interrupted, its return value was: " + result);
+                    } catch (InterruptedException success) {
+                    } catch (Throwable t) { unexpected(t); }
                 }
             };
 
             thread.start();
-            ready.await();
-            Thread.sleep(1000);
+            aboutToWaitFor.await();
             thread.interrupt();
-            done.await();
+            thread.join(10L * 1000L);
+            check(millisElapsedSince(start) < 10L * 1000L);
+            check(!thread.isAlive());
             p.destroy();
         } catch (Throwable t) { unexpected(t); }