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 3f9ad91a975..95a3eb98004 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
@@ -21,6 +21,7 @@ import java.util.Map;
 import java.util.concurrent.atomic.AtomicInteger;
 
 import org.apache.catalina.Container;
+import org.apache.catalina.Context;
 import org.apache.catalina.Engine;
 import org.apache.catalina.LifecycleException;
 import org.apache.catalina.LifecycleState;
@@ -91,6 +92,9 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 			// We can re-throw failure exception directly in the main thread
 			rethrowDeferredStartupExceptions();
 
+			ClassLoader classLoader = findContext().getLoader().getClassLoader();
+			Thread.currentThread().setContextClassLoader(classLoader);
+
 			// Unlike Jetty, all Tomcat threads are daemon threads. We create a
 			// blocking non-daemon to stop immediate shutdown
 			startDaemonAwaitThread();
@@ -101,6 +105,15 @@ public class TomcatEmbeddedServletContainer implements EmbeddedServletContainer
 		}
 	}
 
+	private Context findContext() {
+		for (Container child : this.tomcat.getHost().findChildren()) {
+			if (child instanceof Context) {
+				return (Context) child;
+			}
+		}
+		throw new IllegalStateException("The host does not contain a Context");
+	}
+
 	private void addInstanceIdToEngineName() {
 		int instanceId = containerCounter.incrementAndGet();
 		if (instanceId > 0) {
@@ -245,6 +258,10 @@ 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 cad1a1be231..b2ddd7e12f0 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
@@ -38,6 +38,7 @@ import org.apache.catalina.connector.Connector;
 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.Test;
 import org.mockito.InOrder;
 
@@ -72,6 +73,11 @@ public class TomcatEmbeddedServletContainerFactoryTests
 		return new TomcatEmbeddedServletContainerFactory(0);
 	}
 
+	@After
+	public void restoreTccl() {
+		Thread.currentThread().setContextClassLoader(getClass().getClassLoader());
+	}
+
 	// JMX MBean names clash if you get more than one Engine with the same name...
 	@Test
 	public void tomcatEngineNames() throws Exception {
@@ -358,6 +364,17 @@ public class TomcatEmbeddedServletContainerFactoryTests
 		assertThat(s3.split(":")[0]).as(message).isNotEqualTo(s2.split(":")[1]);
 	}
 
+	@Test
+	public void tcclOfMainThreadIsTomcatWebAppClassLoader() {
+		Thread.currentThread().setContextClassLoader(getClass().getClassLoader());
+		TomcatEmbeddedServletContainerFactory factory = getFactory();
+		this.container = factory.getEmbeddedServletContainer();
+		this.container.start();
+		assertThat(Thread.currentThread().getContextClassLoader())
+				.isInstanceOf(TomcatEmbeddedWebappClassLoader.class);
+		this.container.stop();
+	}
+
 	@Override
 	protected Wrapper getJspServlet() {
 		Container context = ((TomcatEmbeddedServletContainer) this.container).getTomcat()