diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
index 4351a6359e..6e1730d147 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
@@ -223,6 +223,7 @@ public class JettyServletWebServerFactory extends AbstractServletWebServerFactor
 		Configuration[] configurations = getWebAppContextConfigurations(context,
 				initializersToUse);
 		context.setConfigurations(configurations);
+		context.setThrowUnavailableOnStartupException(true);
 		configureSession(context);
 		postProcessWebAppContext(context);
 	}
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
index 6c097fc6c4..e4dfe79798 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
@@ -107,7 +107,7 @@ public class JettyWebServer implements WebServer {
 				this.server.start();
 				this.server.setStopAtShutdown(false);
 			}
-			catch (Exception ex) {
+			catch (Throwable ex) {
 				// Ensure process isn't left running
 				stopSilently();
 				throw new WebServerException("Unable to start embedded Jetty web server",
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
index 2cb9b4381b..69bb99fc6e 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
@@ -20,9 +20,13 @@ import java.net.InetAddress;
 import java.nio.charset.Charset;
 import java.time.Duration;
 import java.util.Arrays;
+import java.util.Collection;
 import java.util.Locale;
 import java.util.Map;
 
+import javax.servlet.ServletContextEvent;
+import javax.servlet.ServletContextListener;
+
 import org.apache.jasper.servlet.JspServlet;
 import org.eclipse.jetty.server.Connector;
 import org.eclipse.jetty.server.Handler;
@@ -41,6 +45,7 @@ import org.mockito.InOrder;
 
 import org.springframework.boot.web.server.PortInUseException;
 import org.springframework.boot.web.server.Ssl;
+import org.springframework.boot.web.server.WebServerException;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactory;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactoryTests;
 
@@ -296,6 +301,42 @@ public class JettyServletWebServerFactoryTests
 				.isEqualTo(localhost.getHostAddress());
 	}
 
+	@Test
+	public void faultyListenerCausesStartFailure() throws Exception {
+		JettyServletWebServerFactory factory = getFactory();
+		factory.addServerCustomizers(new JettyServerCustomizer() {
+
+			@Override
+			public void customize(Server server) {
+				Collection<WebAppContext> contexts = server.getBeans(WebAppContext.class);
+				contexts.iterator().next().addEventListener(new ServletContextListener() {
+
+					@Override
+					public void contextInitialized(ServletContextEvent sce) {
+						throw new RuntimeException();
+					}
+
+					@Override
+					public void contextDestroyed(ServletContextEvent sce) {
+
+					}
+
+				});
+			}
+
+		});
+		this.thrown.expect(WebServerException.class);
+		JettyWebServer jettyWebServer = (JettyWebServer) factory.getWebServer();
+		try {
+			jettyWebServer.start();
+		}
+		finally {
+			QueuedThreadPool threadPool = (QueuedThreadPool) jettyWebServer.getServer()
+					.getThreadPool();
+			assertThat(threadPool.isRunning()).isFalse();
+		}
+	}
+
 	@Override
 	protected JspServlet getJspServlet() throws Exception {
 		WebAppContext context = (WebAppContext) ((JettyWebServer) this.webServer)