diff --git a/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java b/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
index 2d131767f35..252dc5fde13 100644
--- a/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
+++ b/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
@@ -52,7 +52,6 @@ import org.springframework.boot.autoconfigure.web.ServerPropertiesAutoConfigurat
 import org.springframework.boot.autoconfigure.web.WebMvcAutoConfiguration;
 import org.springframework.boot.bind.RelaxedPropertyResolver;
 import org.springframework.boot.context.embedded.AnnotationConfigEmbeddedWebApplicationContext;
-import org.springframework.boot.context.embedded.EmbeddedServletContainerException;
 import org.springframework.boot.context.embedded.EmbeddedWebApplicationContext;
 import org.springframework.context.ApplicationContext;
 import org.springframework.context.ApplicationContextAware;
@@ -141,11 +140,17 @@ public class EndpointWebMvcAutoConfiguration
 			managementPort = ManagementServerPort
 					.get(this.applicationContext.getEnvironment(), this.beanFactory);
 		}
-		if (managementPort == ManagementServerPort.DIFFERENT
-				&& this.applicationContext instanceof EmbeddedWebApplicationContext
-				&& ((EmbeddedWebApplicationContext) this.applicationContext)
-						.getEmbeddedServletContainer() != null) {
-			createChildManagementContext();
+		if (managementPort == ManagementServerPort.DIFFERENT) {
+			if (this.applicationContext instanceof EmbeddedWebApplicationContext
+					&& ((EmbeddedWebApplicationContext) this.applicationContext)
+							.getEmbeddedServletContainer() != null) {
+				createChildManagementContext();
+			}
+			else {
+				logger.warn("Could not start embedded management container on "
+						+ "different port (management endpoints are still available "
+						+ "through JMX)");
+			}
 		}
 		if (managementPort == ManagementServerPort.SAME && this.applicationContext
 				.getEnvironment() instanceof ConfigurableEnvironment) {
@@ -165,24 +170,8 @@ public class EndpointWebMvcAutoConfiguration
 				DispatcherServletAutoConfiguration.class);
 		CloseEventPropagationListener.addIfPossible(this.applicationContext,
 				childContext);
-		try {
-			childContext.refresh();
-			managementContextResolver().setApplicationContext(childContext);
-		}
-		catch (RuntimeException ex) {
-			// No support currently for deploying a war with management.port=<different>,
-			// and this is the signature of that happening
-			if (ex instanceof EmbeddedServletContainerException
-					|| ex.getCause() instanceof EmbeddedServletContainerException) {
-				logger.warn(
-						"Could not start embedded management container (management endpoints "
-								+ "are still available through JMX)");
-				logger.debug("Embedded management container startup failed", ex);
-			}
-			else {
-				throw ex;
-			}
-		}
+		childContext.refresh();
+		managementContextResolver().setApplicationContext(childContext);
 	}
 
 	/**
diff --git a/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java b/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
index 518aa6f9612..e9d718e38aa 100644
--- a/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
+++ b/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
@@ -17,6 +17,8 @@
 package org.springframework.boot.actuate.autoconfigure;
 
 import java.io.FileNotFoundException;
+import java.net.InetSocketAddress;
+import java.net.ServerSocket;
 import java.net.SocketException;
 import java.net.URI;
 import java.nio.charset.Charset;
@@ -30,7 +32,9 @@ import javax.servlet.http.HttpServletResponse;
 import org.hamcrest.Matcher;
 import org.junit.After;
 import org.junit.Before;
+import org.junit.Rule;
 import org.junit.Test;
+import org.junit.rules.ExpectedException;
 import org.springframework.boot.actuate.endpoint.Endpoint;
 import org.springframework.boot.actuate.endpoint.mvc.EndpointHandlerMapping;
 import org.springframework.boot.actuate.endpoint.mvc.EndpointHandlerMappingCustomizer;
@@ -51,6 +55,7 @@ import org.springframework.boot.autoconfigure.web.WebMvcAutoConfiguration;
 import org.springframework.boot.context.embedded.AnnotationConfigEmbeddedWebApplicationContext;
 import org.springframework.boot.context.embedded.ConfigurableEmbeddedServletContainer;
 import org.springframework.boot.context.embedded.EmbeddedServletContainer;
+import org.springframework.boot.context.embedded.EmbeddedServletContainerException;
 import org.springframework.boot.context.embedded.EmbeddedServletContainerInitializedEvent;
 import org.springframework.boot.context.web.ServerPortInfoApplicationContextInitializer;
 import org.springframework.boot.test.EnvironmentTestUtils;
@@ -95,6 +100,9 @@ import static org.mockito.Mockito.mock;
  */
 public class EndpointWebMvcAutoConfigurationTests {
 
+	@Rule
+	public ExpectedException thrown = ExpectedException.none();
+
 	private final AnnotationConfigEmbeddedWebApplicationContext applicationContext = new AnnotationConfigEmbeddedWebApplicationContext();
 
 	private static ThreadLocal<Ports> ports = new ThreadLocal<Ports>();
@@ -234,6 +242,28 @@ public class EndpointWebMvcAutoConfigurationTests {
 		assertAllClosed();
 	}
 
+	@Test
+	public void specificPortsViaPropertiesWithClash() throws Exception {
+		int managementPort = ports.get().management;
+		ServerSocket serverSocket = new ServerSocket();
+		serverSocket.bind(new InetSocketAddress(managementPort));
+		try {
+			EnvironmentTestUtils.addEnvironment(this.applicationContext,
+					"server.port:" + ports.get().server,
+					"management.port:" + ports.get().management);
+			this.applicationContext.register(RootConfig.class, EndpointConfig.class,
+					BaseConfiguration.class, EndpointWebMvcAutoConfiguration.class,
+					ErrorMvcAutoConfiguration.class);
+			this.thrown.expect(EmbeddedServletContainerException.class);
+			this.applicationContext.refresh();
+			this.applicationContext.close();
+		}
+		finally {
+			serverSocket.close();
+			assertAllClosed();
+		}
+	}
+
 	@Test
 	public void contextPath() throws Exception {
 		EnvironmentTestUtils.addEnvironment(this.applicationContext,