diff --git a/spring-boot/src/main/java/org/springframework/boot/context/web/SpringBootServletInitializer.java b/spring-boot/src/main/java/org/springframework/boot/context/web/SpringBootServletInitializer.java
index 89812a95e4..b27f8afad4 100644
--- a/spring-boot/src/main/java/org/springframework/boot/context/web/SpringBootServletInitializer.java
+++ b/spring-boot/src/main/java/org/springframework/boot/context/web/SpringBootServletInitializer.java
@@ -20,6 +20,7 @@ import javax.servlet.Filter;
 import javax.servlet.Servlet;
 import javax.servlet.ServletContext;
 import javax.servlet.ServletContextEvent;
+import javax.servlet.ServletContextListener;
 import javax.servlet.ServletException;
 
 import org.apache.commons.logging.Log;
@@ -62,20 +63,7 @@ public abstract class SpringBootServletInitializer implements WebApplicationInit
 
 	@Override
 	public void onStartup(ServletContext servletContext) throws ServletException {
-		WebApplicationContext rootAppContext = createRootApplicationContext(servletContext);
-		if (rootAppContext != null) {
-			servletContext.addListener(new ContextLoaderListener(rootAppContext) {
-				@Override
-				public void contextInitialized(ServletContextEvent event) {
-					// no-op because the application context is already initialized
-				}
-			});
-		}
-		else {
-			this.logger.debug("No ContextLoaderListener registered, as "
-					+ "createRootApplicationContext() did not "
-					+ "return an application context");
-		}
+		servletContext.addListener(new Listener());
 	}
 
 	protected WebApplicationContext createRootApplicationContext(
@@ -136,4 +124,36 @@ public abstract class SpringBootServletInitializer implements WebApplicationInit
 		return application;
 	}
 
+	/**
+	 * {@link ServletContextListener} used to load the context
+	 */
+	private class Listener implements ServletContextListener {
+
+		private ContextLoaderListener contextLoaderListener;
+
+		@Override
+		public void contextInitialized(ServletContextEvent event) {
+			ServletContext servletContext = event.getServletContext();
+			WebApplicationContext applicationContext = createRootApplicationContext(servletContext);
+			if (applicationContext == null) {
+				SpringBootServletInitializer.this.logger
+						.debug("No ContextLoaderListener registered, as "
+								+ "createRootApplicationContext() did not "
+								+ "return an application context");
+			}
+			else {
+				this.contextLoaderListener = new ContextLoaderListener(applicationContext);
+				// Don't delegate contextInitialized event as we're already setup
+			}
+		}
+
+		@Override
+		public void contextDestroyed(ServletContextEvent event) {
+			if (this.contextLoaderListener != null) {
+				this.contextLoaderListener.contextDestroyed(event);
+			}
+		}
+
+	}
+
 }