diff --git a/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java b/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
index 01bf46eb56c..019f11b2d17 100644
--- a/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
+++ b/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
@@ -94,6 +94,9 @@ public class TomcatWebServer implements WebServer {
 				// Start the server to trigger initialization listeners
 				this.tomcat.start();
 
+				// We can re-throw failure exception directly in the main thread
+				rethrowDeferredStartupExceptions();
+
 				Context context = findContext();
 				try {
 					ContextBindings.bindClassLoader(context, context.getNamingToken(),
@@ -140,6 +143,25 @@ public class TomcatWebServer implements WebServer {
 		}
 	}
 
+	private void rethrowDeferredStartupExceptions() throws Exception {
+		Container[] children = this.tomcat.getHost().findChildren();
+		for (Container container : children) {
+			if (container instanceof TomcatEmbeddedContext) {
+				TomcatStarter tomcatStarter = ((TomcatEmbeddedContext) container)
+						.getStarter();
+				if (tomcatStarter != null) {
+					Exception exception = tomcatStarter.getStartUpException();
+					if (exception != null) {
+						throw exception;
+					}
+				}
+			}
+			if (!LifecycleState.STARTED.equals(container.getState())) {
+				throw new IllegalStateException(container + " failed to start");
+			}
+		}
+	}
+
 	private void startDaemonAwaitThread() {
 		Thread awaitThread = new Thread("container-" + (containerCounter.get())) {
 
diff --git a/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java b/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
index ddc4b0f3572..39d88af3bee 100644
--- a/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
+++ b/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactoryTests.java
@@ -23,7 +23,13 @@ import java.util.Locale;
 import java.util.Map;
 import java.util.concurrent.TimeUnit;
 
+import javax.servlet.Filter;
+import javax.servlet.FilterChain;
+import javax.servlet.FilterConfig;
+import javax.servlet.ServletContext;
 import javax.servlet.ServletException;
+import javax.servlet.ServletRequest;
+import javax.servlet.ServletResponse;
 import javax.servlet.http.HttpServlet;
 import javax.servlet.http.HttpServletRequest;
 import javax.servlet.http.HttpServletResponse;
@@ -45,6 +51,8 @@ import org.mockito.InOrder;
 import org.springframework.boot.web.server.Compression;
 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.ServletContextInitializer;
 import org.springframework.boot.web.servlet.ServletRegistrationBean;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactory;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactoryTests;
@@ -277,6 +285,38 @@ public class JettyServletWebServerFactoryTests
 				.isSameAs(threadPool);
 	}
 
+	@Test
+	public void faultyFilterCausesStartFailure() throws Exception {
+		JettyServletWebServerFactory factory = getFactory();
+		factory.addInitializers(new ServletContextInitializer() {
+
+			@Override
+			public void onStartup(ServletContext servletContext) throws ServletException {
+				servletContext.addFilter("faulty", new Filter() {
+
+					@Override
+					public void init(FilterConfig filterConfig) throws ServletException {
+						throw new ServletException("Faulty filter");
+					}
+
+					@Override
+					public void doFilter(ServletRequest request, ServletResponse response,
+							FilterChain chain) throws IOException, ServletException {
+						chain.doFilter(request, response);
+					}
+
+					@Override
+					public void destroy() {
+					}
+
+				});
+			}
+
+		});
+		this.thrown.expect(WebServerException.class);
+		factory.getWebServer().start();
+	}
+
 	@Override
 	@SuppressWarnings("serial")
 	// Workaround for Jetty issue - https://bugs.eclipse.org/bugs/show_bug.cgi?id=470646
diff --git a/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java b/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
index 8dd392b8010..f96af9f9c13 100644
--- a/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
+++ b/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
@@ -26,7 +26,13 @@ import java.util.concurrent.TimeUnit;
 
 import javax.naming.InitialContext;
 import javax.naming.NamingException;
+import javax.servlet.Filter;
+import javax.servlet.FilterChain;
+import javax.servlet.FilterConfig;
+import javax.servlet.ServletContext;
 import javax.servlet.ServletException;
+import javax.servlet.ServletRequest;
+import javax.servlet.ServletResponse;
 
 import org.apache.catalina.Container;
 import org.apache.catalina.Context;
@@ -51,6 +57,7 @@ import org.mockito.InOrder;
 import org.springframework.boot.testutil.InternalOutputCapture;
 import org.springframework.boot.web.server.Ssl;
 import org.springframework.boot.web.server.WebServerException;
+import org.springframework.boot.web.servlet.ServletContextInitializer;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactory;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactoryTests;
 import org.springframework.test.util.ReflectionTestUtils;
@@ -444,6 +451,38 @@ public class TomcatServletWebServerFactoryTests
 		assertThat(sessionIdGenerator.getJvmRoute()).isEqualTo("test");
 	}
 
+	@Test
+	public void faultyFilterCausesStartFailure() throws Exception {
+		TomcatServletWebServerFactory factory = getFactory();
+		factory.addInitializers(new ServletContextInitializer() {
+
+			@Override
+			public void onStartup(ServletContext servletContext) throws ServletException {
+				servletContext.addFilter("faulty", new Filter() {
+
+					@Override
+					public void init(FilterConfig filterConfig) throws ServletException {
+						throw new ServletException("Faulty filter");
+					}
+
+					@Override
+					public void doFilter(ServletRequest request, ServletResponse response,
+							FilterChain chain) throws IOException, ServletException {
+						chain.doFilter(request, response);
+					}
+
+					@Override
+					public void destroy() {
+					}
+
+				});
+			}
+
+		});
+		this.thrown.expect(WebServerException.class);
+		factory.getWebServer().start();
+	}
+
 	@Override
 	protected JspServlet getJspServlet() throws ServletException {
 		Tomcat tomcat = ((TomcatWebServer) this.webServer).getTomcat();