diff --git a/src/java/org/apache/cassandra/dht/NormalizedRanges.java b/src/java/org/apache/cassandra/dht/NormalizedRanges.java
index c9a040a6585b..2ed17b456393 100644
--- a/src/java/org/apache/cassandra/dht/NormalizedRanges.java
+++ b/src/java/org/apache/cassandra/dht/NormalizedRanges.java
@@ -48,12 +48,12 @@ public class NormalizedRanges<T extends RingPosition<T>> extends AbstractList<Ra
         boolean rangeRightIsMin = range.right.isMinimum();
         boolean keyIsMinimum = key.isMinimum();
 
-        if (keyIsMinimum & rangeRightIsMin)
-            return 0;
+        if (keyIsMinimum)
+            return rangeRightIsMin ? 0 : -1;
 
         int lc = key.compareTo(range.left);
         int rc = key.compareTo(range.right);
-        if ((lc < 0 & !keyIsMinimum) | lc == 0) return 1;
+        if (lc <= 0) return 1;
         if (rc > 0 & !rangeRightIsMin) return -1;
         return 0;
     };
diff --git a/test/unit/org/apache/cassandra/dht/RangeTest.java b/test/unit/org/apache/cassandra/dht/RangeTest.java
index 4c071f3a2637..ec0881541f00 100644
--- a/test/unit/org/apache/cassandra/dht/RangeTest.java
+++ b/test/unit/org/apache/cassandra/dht/RangeTest.java
@@ -860,6 +860,25 @@ else if (ii > 80 && ii <= 90)
         assertEquals(emptyList(), maxLongRange.subtract(ranges));
     }
 
+    @Test
+    @UseMurmur3Partitioner
+    public void testNormalizedRangesWithMinToken()
+    {
+        Token min = t(Long.MIN_VALUE);
+
+        for (NormalizedRanges<Token> ranges : ImmutableList.of(
+            normalizedRanges(ImmutableList.of(r(Long.MIN_VALUE, Long.MIN_VALUE))),
+            normalizedRanges(ImmutableList.of(r(Long.MIN_VALUE, 100))),
+            normalizedRanges(ImmutableList.of(r(100, Long.MIN_VALUE))),
+            normalizedRanges(ImmutableList.of(r(-500, -100), r(100, 500))),
+            normalizedRanges(ImmutableList.of(r(Long.MIN_VALUE, -100), r(100, 500))),
+            normalizedRanges(ImmutableList.of(r(Long.MIN_VALUE, -100), r(100, Long.MIN_VALUE))),
+            normalizedRanges(ImmutableList.of(r(100, 500)))))
+        {
+            assertEquals(Range.isInRanges(min, ranges), ranges.intersects(min));
+        }
+    }
+
     @Test
     public void testExpensiveChecksBurn()
     {