--- old/src/java.base/share/classes/java/time/temporal/ValueRange.java	2020-02-20 14:10:39.000000000 -0800
+++ new/src/java.base/share/classes/java/time/temporal/ValueRange.java	2020-02-20 14:10:38.000000000 -0800
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2012, 2019, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2012, 2020, 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
@@ -145,6 +145,9 @@
      *  or the smallest maximum is greater than the largest maximum
      */
     public static ValueRange of(long min, long maxSmallest, long maxLargest) {
+        if (min > maxSmallest) {
+            throw new IllegalArgumentException("Minimum value must be less than smallest maximum value");
+        }
         return of(min, min, maxSmallest, maxLargest);
     }
 
@@ -160,8 +163,9 @@
      * @return the ValueRange for smallest min, largest min, smallest max, largest max, not null
      * @throws IllegalArgumentException if
      *     the smallest minimum is greater than the smallest maximum,
-     *  or the smallest maximum is greater than the largest maximum
-     *  or the largest minimum is greater than the largest maximum
+     *  or the smallest maximum is greater than the largest maximum,
+     *  or the largest minimum is greater than the largest maximum,
+     *  or the smallest minimum is greater than the largest minimum
      */
     public static ValueRange of(long minSmallest, long minLargest, long maxSmallest, long maxLargest) {
         if (minSmallest > minLargest) {
@@ -171,7 +175,10 @@
             throw new IllegalArgumentException("Smallest maximum value must be less than largest maximum value");
         }
         if (minLargest > maxLargest) {
-            throw new IllegalArgumentException("Minimum value must be less than maximum value");
+            throw new IllegalArgumentException("Largest minimum value must be less than largest maximum value");
+        }
+        if (minSmallest > maxSmallest) {
+            throw new IllegalArgumentException("Smallest minimum value must be less than smallest maximum value");
         }
         return new ValueRange(minSmallest, minLargest, maxSmallest, maxLargest);
     }
--- old/test/jdk/java/time/test/java/time/temporal/TestDateTimeValueRange.java	2020-02-20 14:10:40.000000000 -0800
+++ new/test/jdk/java/time/test/java/time/temporal/TestDateTimeValueRange.java	2020-02-20 14:10:40.000000000 -0800
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2012, 2013, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2012, 2020, 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
@@ -75,6 +75,7 @@
 
 /**
  * Test.
+ * @bug 8239520
  */
 @Test
 public class TestDateTimeValueRange extends AbstractTest {
@@ -138,6 +139,11 @@
         ValueRange.of(1, 31, 28);
     }
 
+    @Test(expectedExceptions = IllegalArgumentException.class)
+    public void test_of_longlonglong_minGtSmallestMax() {
+        ValueRange.of(5, 2, 10);
+    }
+
     //-----------------------------------------------------------------------
     // of(long,long,long,long)
     //-----------------------------------------------------------------------
@@ -178,6 +184,7 @@
                 {2, 1, 28, 31},
                 {2, 1, 31, 28},
                 {12, 13, 1, 2},
+                {5, 5, 2, 10},
         };
     }