diff --git a/spring-restdocs-core/src/main/java/org/springframework/restdocs/payload/JsonContentHandler.java b/spring-restdocs-core/src/main/java/org/springframework/restdocs/payload/JsonContentHandler.java
index 4187b514..a3c4d47d 100644
--- a/spring-restdocs-core/src/main/java/org/springframework/restdocs/payload/JsonContentHandler.java
+++ b/spring-restdocs-core/src/main/java/org/springframework/restdocs/payload/JsonContentHandler.java
@@ -86,8 +86,23 @@ class JsonContentHandler implements ContentHandler {
 		}
 		ExtractedField extracted = this.fieldProcessor.extract(candidate.getPath(),
 				payload);
-		return extracted.getValue() instanceof Collection
-				&& ((Collection<?>) extracted.getValue()).isEmpty();
+		return isEmptyCollection(extracted.getValue());
+	}
+
+	private boolean isEmptyCollection(Object value) {
+		if (!(value instanceof Collection)) {
+			return false;
+		}
+		Collection<?> collection = (Collection<?>) value;
+		if (collection.isEmpty()) {
+			return true;
+		}
+		for (Object entry : collection) {
+			if (!isEmptyCollection(entry)) {
+				return false;
+			}
+		}
+		return true;
 	}
 
 	@Override
diff --git a/spring-restdocs-core/src/test/java/org/springframework/restdocs/payload/JsonContentHandlerTests.java b/spring-restdocs-core/src/test/java/org/springframework/restdocs/payload/JsonContentHandlerTests.java
index ad1d4463..4040300a 100644
--- a/spring-restdocs-core/src/test/java/org/springframework/restdocs/payload/JsonContentHandlerTests.java
+++ b/spring-restdocs-core/src/test/java/org/springframework/restdocs/payload/JsonContentHandlerTests.java
@@ -158,7 +158,7 @@ public class JsonContentHandlerTests {
 	}
 
 	@Test
-	public void describedFieldThatIsSometimesPresentChildOfOptionalArrayIsNotConsideredMissing() {
+	public void describedSometimesPresentFieldThatIsChildOfSometimesPresentOptionalArrayIsNotConsideredMissing() {
 		List<FieldDescriptor> missingFields = new JsonContentHandler(
 				"{\"a\":[ {\"b\": \"bravo\"}, {\"b\": \"bravo\", \"c\": { \"d\": \"delta\"}}]}"
 						.getBytes()).findMissingFields(
@@ -167,4 +167,25 @@ public class JsonContentHandlerTests {
 		assertThat(missingFields.size(), is(equalTo(0)));
 	}
 
+	@Test
+	public void describedMissingFieldThatIsChildOfNestedOptionalArrayThatIsEmptyIsNotConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"a\":[{\"b\":[]}]}".getBytes()).findMissingFields(
+						Arrays.asList(new FieldDescriptor("a.[].b").optional(),
+								new FieldDescriptor("a.[].b.[]").optional(),
+								new FieldDescriptor("a.[].b.[].c")));
+		assertThat(missingFields.size(), is(equalTo(0)));
+	}
+
+	@Test
+	public void describedMissingFieldThatIsChildOfNestedOptionalArrayThatContainsAnObjectIsConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"a\":[{\"b\":[{}]}]}".getBytes()).findMissingFields(
+						Arrays.asList(new FieldDescriptor("a.[].b").optional(),
+								new FieldDescriptor("a.[].b.[]").optional(),
+								new FieldDescriptor("a.[].b.[].c")));
+		assertThat(missingFields.size(), is(equalTo(1)));
+		assertThat(missingFields.get(0).getPath(), is(equalTo("a.[].b.[].c")));
+	}
+
 }