diff --git a/spring-boot-test/src/main/java/org/springframework/boot/test/context/SpringBootTestContextBootstrapper.java b/spring-boot-test/src/main/java/org/springframework/boot/test/context/SpringBootTestContextBootstrapper.java
index 31c5c2fd577..15daa0c9e83 100644
--- a/spring-boot-test/src/main/java/org/springframework/boot/test/context/SpringBootTestContextBootstrapper.java
+++ b/spring-boot-test/src/main/java/org/springframework/boot/test/context/SpringBootTestContextBootstrapper.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2016 the original author or authors.
+ * Copyright 2012-2017 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -19,6 +19,7 @@ package org.springframework.boot.test.context;
 import java.lang.annotation.Annotation;
 import java.util.ArrayList;
 import java.util.Arrays;
+import java.util.HashSet;
 import java.util.List;
 import java.util.Set;
 
@@ -28,9 +29,12 @@ import org.apache.commons.logging.LogFactory;
 import org.springframework.boot.SpringBootConfiguration;
 import org.springframework.boot.test.context.SpringBootTest.WebEnvironment;
 import org.springframework.core.annotation.AnnotatedElementUtils;
+import org.springframework.core.annotation.AnnotationUtils;
 import org.springframework.core.env.Environment;
 import org.springframework.core.io.support.SpringFactoriesLoader;
+import org.springframework.test.context.ContextConfiguration;
 import org.springframework.test.context.ContextConfigurationAttributes;
+import org.springframework.test.context.ContextHierarchy;
 import org.springframework.test.context.ContextLoader;
 import org.springframework.test.context.MergedContextConfiguration;
 import org.springframework.test.context.TestContext;
@@ -137,7 +141,7 @@ public class SpringBootTestContextBootstrapper extends DefaultTestContextBootstr
 				propertySourceProperties
 						.toArray(new String[propertySourceProperties.size()]));
 		WebEnvironment webEnvironment = getWebEnvironment(mergedConfig.getTestClass());
-		if (webEnvironment != null) {
+		if (webEnvironment != null && isWebEnvironmentSupported(mergedConfig)) {
 			if (webEnvironment.isEmbedded() || (webEnvironment == WebEnvironment.MOCK
 					&& hasWebEnvironmentClasses())) {
 				WebAppConfiguration webAppConfiguration = AnnotatedElementUtils
@@ -152,6 +156,32 @@ public class SpringBootTestContextBootstrapper extends DefaultTestContextBootstr
 		return mergedConfig;
 	}
 
+	private boolean isWebEnvironmentSupported(MergedContextConfiguration mergedConfig) {
+		Class<?> testClass = mergedConfig.getTestClass();
+		ContextHierarchy hierarchy = AnnotationUtils.getAnnotation(testClass,
+				ContextHierarchy.class);
+		if (hierarchy == null || hierarchy.value().length == 0) {
+			return true;
+		}
+		ContextConfiguration[] configurations = hierarchy.value();
+		return isFromConfiguration(mergedConfig,
+				configurations[configurations.length - 1]);
+	}
+
+	private boolean isFromConfiguration(MergedContextConfiguration candidateConfig,
+			ContextConfiguration configuration) {
+		ContextConfigurationAttributes attributes = new ContextConfigurationAttributes(
+				candidateConfig.getTestClass(), configuration);
+		Set<Class<?>> configurationClasses = new HashSet<Class<?>>(
+				Arrays.asList(attributes.getClasses()));
+		for (Class<?> candidate : candidateConfig.getClasses()) {
+			if (configurationClasses.contains(candidate)) {
+				return true;
+			}
+		}
+		return false;
+	}
+
 	private boolean hasWebEnvironmentClasses() {
 		for (String className : WEB_ENVIRONMENT_CLASSES) {
 			if (!ClassUtils.isPresent(className, null)) {
diff --git a/spring-boot-test/src/test/java/org/springframework/boot/test/context/SpringBootTestWebEnvironmentContextHierarchyTests.java b/spring-boot-test/src/test/java/org/springframework/boot/test/context/SpringBootTestWebEnvironmentContextHierarchyTests.java
new file mode 100644
index 00000000000..e506577a662
--- /dev/null
+++ b/spring-boot-test/src/test/java/org/springframework/boot/test/context/SpringBootTestWebEnvironmentContextHierarchyTests.java
@@ -0,0 +1,75 @@
+/*
+ * Copyright 2012-2017 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.test.context;
+
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.test.context.AbstractSpringBootTestEmbeddedWebEnvironmentTests.AbstractConfig;
+import org.springframework.boot.test.context.SpringBootTest.WebEnvironment;
+import org.springframework.boot.test.context.SpringBootTestWebEnvironmentContextHierarchyTests.ChildConfiguration;
+import org.springframework.boot.test.context.SpringBootTestWebEnvironmentContextHierarchyTests.ParentConfiguration;
+import org.springframework.context.ApplicationContext;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.test.annotation.DirtiesContext;
+import org.springframework.test.context.ContextConfiguration;
+import org.springframework.test.context.ContextHierarchy;
+import org.springframework.test.context.junit4.SpringRunner;
+import org.springframework.web.bind.annotation.RestController;
+import org.springframework.web.context.WebApplicationContext;
+import org.springframework.web.servlet.config.annotation.EnableWebMvc;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Tests for {@link SpringBootTest} configured with {@link WebEnvironment#DEFINED_PORT}.
+ *
+ * @author Phillip Webb
+ * @author Andy Wilkinson
+ */
+@RunWith(SpringRunner.class)
+@DirtiesContext
+@SpringBootTest(webEnvironment = WebEnvironment.DEFINED_PORT, properties = {
+		"server.port=0", "value=123" })
+@ContextHierarchy({ @ContextConfiguration(classes = ParentConfiguration.class),
+		@ContextConfiguration(classes = ChildConfiguration.class) })
+public class SpringBootTestWebEnvironmentContextHierarchyTests {
+
+	@Autowired
+	private ApplicationContext context;
+
+	@Test
+	public void testShouldOnlyStartSingleServer() throws Exception {
+		ApplicationContext parent = this.context.getParent();
+		assertThat(this.context).isInstanceOf(WebApplicationContext.class);
+		assertThat(parent).isNotInstanceOf(WebApplicationContext.class);
+	}
+
+	@Configuration
+	protected static class ParentConfiguration extends AbstractConfig {
+
+	}
+
+	@Configuration
+	@EnableWebMvc
+	@RestController
+	protected static class ChildConfiguration extends AbstractConfig {
+
+	}
+
+}