diff --git a/server/src/main/java/org/elasticsearch/ElasticsearchException.java b/server/src/main/java/org/elasticsearch/ElasticsearchException.java
index b1c02c4ac2718..929c5f49e344f 100644
--- a/server/src/main/java/org/elasticsearch/ElasticsearchException.java
+++ b/server/src/main/java/org/elasticsearch/ElasticsearchException.java
@@ -31,6 +31,7 @@
 import org.elasticsearch.common.logging.LoggerMessageFormat;
 import org.elasticsearch.common.xcontent.ToXContentFragment;
 import org.elasticsearch.common.xcontent.XContentBuilder;
+import org.elasticsearch.common.xcontent.XContentParseException;
 import org.elasticsearch.common.xcontent.XContentParser;
 import org.elasticsearch.index.Index;
 import org.elasticsearch.index.shard.ShardId;
@@ -635,8 +636,25 @@ public ElasticsearchException[] guessRootCauses() {
     public static ElasticsearchException[] guessRootCauses(Throwable t) {
         Throwable ex = ExceptionsHelper.unwrapCause(t);
         if (ex instanceof ElasticsearchException) {
+            // ElasticsearchException knows how to guess its own root cause
             return ((ElasticsearchException) ex).guessRootCauses();
         }
+        if (ex instanceof XContentParseException) {
+            /*
+             * We'd like to unwrap parsing exceptions to the inner-most
+             * parsing exception because that is generally the most interesting
+             * exception to return to the user. If that exception is caused by
+             * an ElasticsearchException we'd like to keep unwrapping because
+             * ElasticserachExceptions tend to contain useful information for
+             * the user.
+             */
+            Throwable cause = ex.getCause();
+            if (cause != null) {
+                if (cause instanceof XContentParseException || cause instanceof ElasticsearchException) {
+                    return guessRootCauses(ex.getCause());
+                }
+            }
+        }
         return new ElasticsearchException[]{new ElasticsearchException(t.getMessage(), t) {
             @Override
             protected String getExceptionName() {
diff --git a/server/src/main/java/org/elasticsearch/ElasticsearchWrapperException.java b/server/src/main/java/org/elasticsearch/ElasticsearchWrapperException.java
index 0b809e0923b62..7e0fd3a24cb09 100644
--- a/server/src/main/java/org/elasticsearch/ElasticsearchWrapperException.java
+++ b/server/src/main/java/org/elasticsearch/ElasticsearchWrapperException.java
@@ -19,7 +19,11 @@
 
 package org.elasticsearch;
 
+/**
+ * An exception that is meant to be "unwrapped" when sent back to the user
+ * as an error because its is {@link #getCause() cause}, if non-null is
+ * <strong>always</strong> more useful to the user than the exception itself.
+ */
 public interface ElasticsearchWrapperException {
-
     Throwable getCause();
 }
diff --git a/server/src/test/java/org/elasticsearch/ElasticsearchExceptionTests.java b/server/src/test/java/org/elasticsearch/ElasticsearchExceptionTests.java
index d3560fc6db355..6e4c97fd3dad2 100644
--- a/server/src/test/java/org/elasticsearch/ElasticsearchExceptionTests.java
+++ b/server/src/test/java/org/elasticsearch/ElasticsearchExceptionTests.java
@@ -41,6 +41,7 @@
 import org.elasticsearch.common.xcontent.XContentFactory;
 import org.elasticsearch.common.xcontent.XContentHelper;
 import org.elasticsearch.common.xcontent.XContentLocation;
+import org.elasticsearch.common.xcontent.XContentParseException;
 import org.elasticsearch.common.xcontent.XContentParser;
 import org.elasticsearch.common.xcontent.XContentType;
 import org.elasticsearch.discovery.DiscoverySettings;
@@ -78,6 +79,7 @@
 import static org.hamcrest.CoreMatchers.hasItems;
 import static org.hamcrest.Matchers.equalTo;
 import static org.hamcrest.Matchers.hasSize;
+import static org.hamcrest.Matchers.instanceOf;
 import static org.hamcrest.Matchers.startsWith;
 
 public class ElasticsearchExceptionTests extends ESTestCase {
@@ -124,13 +126,13 @@ public void testGuessRootCause() {
             } else {
                 rootCauses = ElasticsearchException.guessRootCauses(randomBoolean() ? new RemoteTransportException("remoteboom", ex) : ex);
             }
-            assertEquals(ElasticsearchException.getExceptionName(rootCauses[0]), "parsing_exception");
-            assertEquals(rootCauses[0].getMessage(), "foobar");
+            assertEquals("parsing_exception", ElasticsearchException.getExceptionName(rootCauses[0]));
+            assertEquals("foobar", rootCauses[0].getMessage());
 
             ElasticsearchException oneLevel = new ElasticsearchException("foo", new RuntimeException("foobar"));
             rootCauses = oneLevel.guessRootCauses();
-            assertEquals(ElasticsearchException.getExceptionName(rootCauses[0]), "exception");
-            assertEquals(rootCauses[0].getMessage(), "foo");
+            assertEquals("exception", ElasticsearchException.getExceptionName(rootCauses[0]));
+            assertEquals("foo", rootCauses[0].getMessage());
         }
         {
             ShardSearchFailure failure = new ShardSearchFailure(
@@ -146,20 +148,40 @@ public void testGuessRootCause() {
             assertEquals(rootCauses.length, 2);
             assertEquals(ElasticsearchException.getExceptionName(rootCauses[0]), "parsing_exception");
             assertEquals(rootCauses[0].getMessage(), "foobar");
-            assertEquals(((ParsingException) rootCauses[0]).getLineNumber(), 1);
-            assertEquals(((ParsingException) rootCauses[0]).getColumnNumber(), 2);
-            assertEquals(ElasticsearchException.getExceptionName(rootCauses[1]), "query_shard_exception");
-            assertEquals((rootCauses[1]).getIndex().getName(), "foo1");
-            assertEquals(rootCauses[1].getMessage(), "foobar");
+            assertEquals(1, ((ParsingException) rootCauses[0]).getLineNumber());
+            assertEquals(2, ((ParsingException) rootCauses[0]).getColumnNumber());
+            assertEquals("query_shard_exception", ElasticsearchException.getExceptionName(rootCauses[1]));
+            assertEquals("foo1", rootCauses[1].getIndex().getName());
+            assertEquals("foobar", rootCauses[1].getMessage());
         }
 
         {
             final ElasticsearchException[] foobars = ElasticsearchException.guessRootCauses(new IllegalArgumentException("foobar"));
             assertEquals(foobars.length, 1);
-            assertTrue(foobars[0] instanceof ElasticsearchException);
-            assertEquals(foobars[0].getMessage(), "foobar");
-            assertEquals(foobars[0].getCause().getClass(), IllegalArgumentException.class);
-            assertEquals(foobars[0].getExceptionName(), "illegal_argument_exception");
+            assertThat(foobars[0], instanceOf(ElasticsearchException.class));
+            assertEquals("foobar", foobars[0].getMessage());
+            assertEquals(IllegalArgumentException.class, foobars[0].getCause().getClass());
+            assertEquals("illegal_argument_exception", foobars[0].getExceptionName());
+        }
+
+        {
+            XContentParseException inner = new XContentParseException(null, "inner");
+            XContentParseException outer = new XContentParseException(null, "outer", inner);
+            final ElasticsearchException[] causes = ElasticsearchException.guessRootCauses(outer);
+            assertEquals(causes.length, 1);
+            assertThat(causes[0], instanceOf(ElasticsearchException.class));
+            assertEquals("inner", causes[0].getMessage());
+            assertEquals("x_content_parse_exception", causes[0].getExceptionName());
+        }
+
+        {
+            ElasticsearchException inner = new ElasticsearchException("inner");
+            XContentParseException outer = new XContentParseException(null, "outer", inner);
+            final ElasticsearchException[] causes = ElasticsearchException.guessRootCauses(outer);
+            assertEquals(causes.length, 1);
+            assertThat(causes[0], instanceOf(ElasticsearchException.class));
+            assertEquals("inner", causes[0].getMessage());
+            assertEquals("exception", causes[0].getExceptionName());
         }
     }