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 afacb6e1..86dbd7b4 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
@@ -52,8 +52,10 @@ class JsonContentHandler implements ContentHandler {
 		List<FieldDescriptor> missingFields = new ArrayList<>();
 		Object payload = readContent();
 		for (FieldDescriptor fieldDescriptor : fieldDescriptors) {
-			if (!fieldDescriptor.isOptional() && !this.fieldProcessor
-					.hasField(fieldDescriptor.getPath(), payload)) {
+			if (!fieldDescriptor.isOptional()
+					&& !this.fieldProcessor.hasField(fieldDescriptor.getPath(), payload)
+					&& !isNestedBeneathMissingOptionalField(fieldDescriptor,
+							fieldDescriptors, payload)) {
 				missingFields.add(fieldDescriptor);
 			}
 		}
@@ -61,6 +63,20 @@ class JsonContentHandler implements ContentHandler {
 		return missingFields;
 	}
 
+	private boolean isNestedBeneathMissingOptionalField(FieldDescriptor missing,
+			List<FieldDescriptor> fieldDescriptors, Object payload) {
+		List<FieldDescriptor> candidates = new ArrayList<>(fieldDescriptors);
+		candidates.remove(missing);
+		for (FieldDescriptor candidate : candidates) {
+			if (candidate.isOptional()
+					&& missing.getPath().startsWith(candidate.getPath())
+					&& !this.fieldProcessor.hasField(candidate.getPath(), payload)) {
+				return true;
+			}
+		}
+		return false;
+	}
+
 	@Override
 	public String getUndocumentedContent(List<FieldDescriptor> fieldDescriptors) {
 		Object content = readContent();
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 b2e5a582..e275bd92 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
@@ -17,6 +17,8 @@
 package org.springframework.restdocs.payload;
 
 import java.io.IOException;
+import java.util.Arrays;
+import java.util.List;
 
 import org.junit.Rule;
 import org.junit.Test;
@@ -107,4 +109,42 @@ public class JsonContentHandlerTests {
 		new JsonContentHandler("Non-JSON content".getBytes());
 	}
 
+	@Test
+	public void describedFieldThatIsNotPresentIsConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"a\": \"alpha\", \"b\":\"bravo\"}".getBytes())
+						.findMissingFields(Arrays.asList(new FieldDescriptor("a"),
+								new FieldDescriptor("b"), new FieldDescriptor("c")));
+		assertThat(missingFields.size(), is(equalTo(1)));
+		assertThat(missingFields.get(0).getPath(), is(equalTo("c")));
+	}
+
+	@Test
+	public void describedOptionalFieldThatIsNotPresentIsNotConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"a\": \"alpha\", \"b\":\"bravo\"}".getBytes()).findMissingFields(
+						Arrays.asList(new FieldDescriptor("a"), new FieldDescriptor("b"),
+								new FieldDescriptor("c").optional()));
+		assertThat(missingFields.size(), is(equalTo(0)));
+	}
+
+	@Test
+	public void describedFieldThatIsNotPresentNestedBeneathOptionalFieldThatIsPresentIsConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"a\":\"alpha\",\"b\":\"bravo\"}".getBytes()).findMissingFields(
+						Arrays.asList(new FieldDescriptor("a").optional(),
+								new FieldDescriptor("b"), new FieldDescriptor("a.c")));
+		assertThat(missingFields.size(), is(equalTo(1)));
+		assertThat(missingFields.get(0).getPath(), is(equalTo("a.c")));
+	}
+
+	@Test
+	public void describedFieldThatIsNotPresentNestedBeneathOptionalFieldThatIsNotPresentIsNotConsideredMissing() {
+		List<FieldDescriptor> missingFields = new JsonContentHandler(
+				"{\"b\":\"bravo\"}".getBytes()).findMissingFields(
+						Arrays.asList(new FieldDescriptor("a").optional(),
+								new FieldDescriptor("b"), new FieldDescriptor("a.c")));
+		assertThat(missingFields.size(), is(equalTo(0)));
+	}
+
 }