diff --git a/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedServletContainerFactory.java b/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedServletContainerFactory.java
index b4c32f7a315..42bd98c1f9a 100644
--- a/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedServletContainerFactory.java
+++ b/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedServletContainerFactory.java
@@ -34,6 +34,7 @@ import org.apache.catalina.core.StandardContext;
 import org.apache.catalina.core.StandardEngine;
 import org.apache.catalina.core.StandardHost;
 import org.apache.catalina.core.StandardService;
+import org.apache.catalina.loader.WebappLoader;
 import org.apache.catalina.startup.Tomcat;
 import org.apache.catalina.startup.Tomcat.FixContextListener;
 import org.apache.coyote.AbstractProtocol;
@@ -139,9 +140,12 @@ public class TomcatEmbeddedServletContainerFactory extends
 		context.setPath(getContextPath());
 		context.setDocBase(docBase.getAbsolutePath());
 		context.addLifecycleListener(new FixContextListener());
-		if (this.resourceLoader != null) {
-			context.setParentClassLoader(this.resourceLoader.getClassLoader());
-		}
+		context.setParentClassLoader(this.resourceLoader != null ? this.resourceLoader
+				.getClassLoader() : ClassUtils.getDefaultClassLoader());
+		WebappLoader loader = new WebappLoader(context.getParentClassLoader());
+		loader.setLoaderClass(TomcatEmbeddedWebappClassLoader.class.getName());
+		context.setLoader(loader);
+
 		if (isRegisterDefaultServlet()) {
 			addDefaultServlet(context);
 		}
diff --git a/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedWebappClassLoader.java b/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedWebappClassLoader.java
new file mode 100644
index 00000000000..6b81c3fd13b
--- /dev/null
+++ b/spring-bootstrap/src/main/java/org/springframework/bootstrap/context/embedded/tomcat/TomcatEmbeddedWebappClassLoader.java
@@ -0,0 +1,59 @@
+/*
+ * Copyright 2012-2013 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.bootstrap.context.embedded.tomcat;
+
+import java.net.URL;
+import java.net.URLClassLoader;
+
+import org.apache.catalina.loader.WebappClassLoader;
+
+/**
+ * Extension of Tomcat's {@link WebappClassLoader} that does not consider the
+ * {@link ClassLoader#getSystemClassLoader() system classloader}. This is required to to
+ * ensure that any custom context classloader is always used (as is the case with some
+ * executable archives).
+ * 
+ * @author Phillip Webb
+ */
+public class TomcatEmbeddedWebappClassLoader extends WebappClassLoader {
+
+	public TomcatEmbeddedWebappClassLoader() {
+		super();
+		this.system = new EmbeddedSystemClassLoader();
+	}
+
+	public TomcatEmbeddedWebappClassLoader(ClassLoader parent) {
+		super(parent);
+		this.system = new EmbeddedSystemClassLoader();
+	}
+
+	private static class EmbeddedSystemClassLoader extends URLClassLoader {
+
+		public EmbeddedSystemClassLoader() {
+			super(new URL[] {});
+		}
+
+		@Override
+		public Class<?> loadClass(String name) throws ClassNotFoundException {
+			throw new ClassNotFoundException(
+					"System ClassLoader disabled for embedded context, unable to load "
+							+ name);
+		}
+
+	}
+
+}