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 91ef1ed4e9..90810cb4a9 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
@@ -155,6 +155,7 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 			}
 
 		};
+		awaitThread.setContextClassLoader(getClass().getClassLoader());
 		awaitThread.setDaemon(false);
 		awaitThread.start();
 	}
@@ -191,13 +192,21 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 
 	private void stopSilently() {
 		try {
-			this.tomcat.stop();
+			stopTomcat();
 		}
 		catch (LifecycleException ex) {
 			// Ignore
 		}
 	}
 
+	private void stopTomcat() throws LifecycleException {
+		if (Thread.currentThread()
+				.getContextClassLoader() instanceof TomcatEmbeddedWebappClassLoader) {
+			Thread.currentThread().setContextClassLoader(getClass().getClassLoader());
+		}
+		this.tomcat.stop();
+	}
+
 	private void addPreviouslyRemovedConnectors() {
 		Service[] services = this.tomcat.getServer().findServices();
 		for (Service service : services) {
@@ -246,7 +255,7 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 	public synchronized void stop() throws EmbeddedServletContainerException {
 		try {
 			try {
-				this.tomcat.stop();
+				stopTomcat();
 				this.tomcat.destroy();
 			}
 			catch (LifecycleException ex) {
@@ -258,10 +267,6 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 					ex);
 		}
 		finally {
-			if (Thread.currentThread()
-					.getContextClassLoader() instanceof TomcatEmbeddedWebappClassLoader) {
-				Thread.currentThread().setContextClassLoader(getClass().getClassLoader());
-			}
 			containerCounter.decrementAndGet();
 		}
 	}
diff --git a/spring-boot/src/test/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainerFactoryTests.java b/spring-boot/src/test/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainerFactoryTests.java
index bbc0c1aa6a..4c160715c1 100644
--- a/spring-boot/src/test/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainerFactoryTests.java
+++ b/spring-boot/src/test/java/org/springframework/boot/context/embedded/tomcat/TomcatEmbeddedServletContainerFactoryTests.java
@@ -37,6 +37,7 @@ import org.apache.catalina.startup.Tomcat;
 import org.apache.catalina.valves.RemoteIpValve;
 import org.apache.coyote.http11.AbstractHttp11JsseProtocol;
 import org.junit.After;
+import org.junit.Rule;
 import org.junit.Test;
 import org.mockito.InOrder;
 
@@ -44,6 +45,7 @@ import org.springframework.boot.context.embedded.AbstractEmbeddedServletContaine
 import org.springframework.boot.context.embedded.AbstractEmbeddedServletContainerFactoryTests;
 import org.springframework.boot.context.embedded.EmbeddedServletContainerException;
 import org.springframework.boot.context.embedded.Ssl;
+import org.springframework.boot.testutil.OutputCapture;
 import org.springframework.test.util.ReflectionTestUtils;
 import org.springframework.util.SocketUtils;
 
@@ -67,6 +69,9 @@ import static org.mockito.Mockito.verify;
 public class TomcatEmbeddedServletContainerFactoryTests
 		extends AbstractEmbeddedServletContainerFactoryTests {
 
+	@Rule
+	public OutputCapture outputCapture = new OutputCapture();
+
 	@Override
 	protected TomcatEmbeddedServletContainerFactory getFactory() {
 		return new TomcatEmbeddedServletContainerFactory(0);
@@ -335,6 +340,16 @@ public class TomcatEmbeddedServletContainerFactoryTests
 
 	}
 
+	@Test
+	public void startupFailureDoesNotResultInUnstoppedThreadsBeingReported()
+			throws IOException {
+		super.portClashOfPrimaryConnectorResultsInPortInUseException();
+
+		String string = this.outputCapture.toString();
+		assertThat(string)
+				.doesNotContain("appears to have started a thread named [main]");
+	}
+
 	@Override
 	protected void addConnector(int port,
 			AbstractEmbeddedServletContainerFactory factory) {