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 008f6366..0f2932f8 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
@@ -75,7 +75,7 @@ private boolean isNestedBeneathMissingOptionalField(FieldDescriptor descriptor,
 		List<FieldDescriptor> candidates = new ArrayList<>(this.fieldDescriptors);
 		candidates.remove(descriptor);
 		for (FieldDescriptor candidate : candidates) {
-			if (candidate.isOptional() && descriptor.getPath().startsWith(candidate.getPath())
+			if (candidate.isOptional() && isNestedBeneath(candidate.getPath(), descriptor.getPath())
 					&& isMissing(candidate, payload)) {
 				return true;
 			}
@@ -83,6 +83,10 @@ && isMissing(candidate, payload)) {
 		return false;
 	}
 
+	private boolean isNestedBeneath(String ancestorPath, String path) {
+		return path.equals(ancestorPath) || path.startsWith(ancestorPath + ".") || path.startsWith(ancestorPath + "[");
+	}
+
 	private boolean isMissing(FieldDescriptor candidate, Object payload) {
 		if (!this.fieldProcessor.hasField(candidate.getPath(), payload)) {
 			return true;
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 de61f3be..e421ab31 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
@@ -158,6 +158,26 @@ void describedFieldThatIsNotPresentNestedBeneathOptionalFieldThatIsNotPresentIsN
 		assertThat(missingFields.size()).isEqualTo(0);
 	}
 
+	@Test
+	void describedFieldThatIsNotPresentWithPathPrefixedByPathOfMissingOptionalFieldIsConsideredMissing() {
+		List<FieldDescriptor> descriptors = Arrays.asList(new FieldDescriptor("a").optional(),
+				new FieldDescriptor("ab"));
+		List<FieldDescriptor> missingFields = new JsonContentHandler("{\"c\":\"charlie\"}".getBytes(), descriptors)
+			.findMissingFields();
+		assertThat(missingFields.size()).isEqualTo(1);
+		assertThat(missingFields.get(0).getPath()).isEqualTo("ab");
+	}
+
+	@Test
+	void describedNestedFieldThatIsNotPresentWithPathPrefixedByPathOfMissingOptionalFieldIsConsideredMissing() {
+		List<FieldDescriptor> descriptors = Arrays.asList(new FieldDescriptor("a.b").optional(),
+				new FieldDescriptor("a.bc"));
+		List<FieldDescriptor> missingFields = new JsonContentHandler("{\"a\":{}}".getBytes(), descriptors)
+			.findMissingFields();
+		assertThat(missingFields.size()).isEqualTo(1);
+		assertThat(missingFields.get(0).getPath()).isEqualTo("a.bc");
+	}
+
 	@Test
 	void describedFieldThatIsNotPresentNestedBeneathOptionalArrayThatIsEmptyIsNotConsideredMissing() {
 		List<FieldDescriptor> descriptors = Arrays.asList(new FieldDescriptor("outer"),