diff --git a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesAutoConfigurationTests.java b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesAutoConfigurationTests.java
index 9d3fb42c0a2..747055692d2 100644
--- a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesAutoConfigurationTests.java
+++ b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesAutoConfigurationTests.java
@@ -24,7 +24,6 @@ import org.junit.Rule;
 import org.junit.Test;
 import org.junit.rules.ExpectedException;
 import org.mockito.Mockito;
-import org.springframework.beans.factory.BeanCreationException;
 import org.springframework.boot.TestUtils;
 import org.springframework.boot.autoconfigure.PropertyPlaceholderAutoConfiguration;
 import org.springframework.boot.context.embedded.AnnotationConfigEmbeddedWebApplicationContext;
@@ -35,6 +34,7 @@ import org.springframework.boot.context.embedded.EmbeddedServletContainerFactory
 import org.springframework.boot.context.embedded.jetty.JettyEmbeddedServletContainerFactory;
 import org.springframework.boot.context.embedded.properties.ServerProperties;
 import org.springframework.boot.context.embedded.tomcat.TomcatEmbeddedServletContainerFactory;
+import org.springframework.context.ApplicationContextException;
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
 
@@ -133,7 +133,7 @@ public class ServerPropertiesAutoConfigurationTests {
 		this.context.register(Config.class, MutiServerPropertiesBeanConfig.class,
 				ServerPropertiesAutoConfiguration.class,
 				PropertyPlaceholderAutoConfiguration.class);
-		this.thrown.expect(BeanCreationException.class);
+		this.thrown.expect(ApplicationContextException.class);
 		this.thrown.expectMessage("Multiple ServerProperties");
 		this.context.refresh();
 	}
diff --git a/spring-boot/src/main/java/org/springframework/boot/context/embedded/EmbeddedWebApplicationContext.java b/spring-boot/src/main/java/org/springframework/boot/context/embedded/EmbeddedWebApplicationContext.java
index 16026485001..d9139f237d3 100644
--- a/spring-boot/src/main/java/org/springframework/boot/context/embedded/EmbeddedWebApplicationContext.java
+++ b/spring-boot/src/main/java/org/springframework/boot/context/embedded/EmbeddedWebApplicationContext.java
@@ -131,7 +131,13 @@ public class EmbeddedWebApplicationContext extends GenericWebApplicationContext
 	protected void onRefresh() {
 		super.onRefresh();
 		registerShutdownHook();
-		createEmbeddedServletContainer();
+		try {
+			createEmbeddedServletContainer();
+		}
+		catch (Throwable ex) {
+			throw new ApplicationContextException("Unable to start embedded container",
+					ex);
+		}
 	}
 
 	@Override
diff --git a/spring-boot/src/main/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainer.java b/spring-boot/src/main/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainer.java
index d3303b39533..a2e1116cdc1 100644
--- a/spring-boot/src/main/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainer.java
+++ b/spring-boot/src/main/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainer.java
@@ -17,6 +17,7 @@
 package org.springframework.boot.context.embedded.tomcat;
 
 import org.apache.catalina.LifecycleException;
+import org.apache.catalina.LifecycleState;
 import org.apache.catalina.connector.Connector;
 import org.apache.catalina.startup.Tomcat;
 import org.apache.commons.logging.Log;
@@ -75,6 +76,10 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 			};
 			awaitThread.setDaemon(false);
 			awaitThread.start();
+			if (LifecycleState.FAILED.equals(this.tomcat.getConnector().getState())) {
+				this.tomcat.stop();
+				throw new IllegalStateException("Tomcat connector in failed state");
+			}
 		}
 		catch (Exception ex) {
 			throw new EmbeddedServletContainerException(