diff --git a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/LaunchedURLClassLoader.java b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/LaunchedURLClassLoader.java
index b8e7a272464..f9bfac9b2b2 100644
--- a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/LaunchedURLClassLoader.java
+++ b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/LaunchedURLClassLoader.java
@@ -17,8 +17,10 @@
 package org.springframework.boot.loader;
 
 import java.io.IOException;
+import java.net.JarURLConnection;
 import java.net.URL;
 import java.net.URLClassLoader;
+import java.net.URLConnection;
 import java.security.AccessController;
 import java.security.PrivilegedExceptionAction;
 import java.util.Arrays;
@@ -228,6 +230,30 @@ public class LaunchedURLClassLoader extends URLClassLoader {
 		}
 	}
 
+	/**
+	 * Clear URL caches.
+	 */
+	public void clearCache() {
+		for (URL url : getURLs()) {
+			try {
+				URLConnection connection = url.openConnection();
+				if (connection instanceof JarURLConnection) {
+					clearCache(connection);
+				}
+			}
+			catch (IOException ex) {
+			}
+		}
+
+	}
+
+	private void clearCache(URLConnection connection) throws IOException {
+		Object jarFile = ((JarURLConnection) connection).getJarFile();
+		if (jarFile instanceof JarFile) {
+			((JarFile) jarFile).clearCache();
+		}
+	}
+
 	@UsesJava7
 	private static LockProvider setupLockProvider() {
 		try {
diff --git a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
index b9a23927a6e..6fb02a4af79 100644
--- a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
+++ b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
@@ -347,6 +347,10 @@ public class JarFile extends java.util.jar.JarFile {
 		}
 	}
 
+	public void clearCache() {
+		this.entries.clearCache();
+	}
+
 	/**
 	 * Register a {@literal 'java.protocol.handler.pkgs'} property so that a
 	 * {@link URLStreamHandler} will be located to deal with jar URLs.
diff --git a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileEntries.java b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileEntries.java
index d70c7b6863b..e577cfb45d9 100644
--- a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileEntries.java
+++ b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileEntries.java
@@ -270,6 +270,10 @@ class JarFileEntries implements CentralDirectoryVistor, Iterable<JarEntry> {
 		return index;
 	}
 
+	public void clearCache() {
+		this.entriesCache.clear();
+	}
+
 	private AsciiBytes applyFilter(AsciiBytes name) {
 		return (this.filter == null ? name : this.filter.apply(name));
 	}
diff --git a/spring-boot/src/main/java/org/springframework/boot/ClearCachesApplicationListener.java b/spring-boot/src/main/java/org/springframework/boot/ClearCachesApplicationListener.java
new file mode 100644
index 00000000000..83ec2c389bb
--- /dev/null
+++ b/spring-boot/src/main/java/org/springframework/boot/ClearCachesApplicationListener.java
@@ -0,0 +1,54 @@
+/*
+ * Copyright 2012-2015 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.boot;
+
+import java.lang.reflect.Method;
+
+import org.springframework.context.ApplicationListener;
+import org.springframework.context.event.ContextRefreshedEvent;
+import org.springframework.util.ReflectionUtils;
+
+/**
+ * {@link ApplicationListener} to cleanup caches once the context is loaded.
+ *
+ * @author Phillip Webb
+ */
+class ClearCachesApplicationListener
+		implements ApplicationListener<ContextRefreshedEvent> {
+
+	@Override
+	public void onApplicationEvent(ContextRefreshedEvent event) {
+		ReflectionUtils.clearCache();
+		clearClassLoaderCaches(Thread.currentThread().getContextClassLoader());
+	}
+
+	private void clearClassLoaderCaches(ClassLoader classLoader) {
+		if (classLoader == null) {
+			return;
+		}
+		try {
+			Method clearCacheMethod = classLoader.getClass()
+					.getDeclaredMethod("clearCache");
+			clearCacheMethod.invoke(classLoader);
+		}
+		catch (Exception ex) {
+			// Ignore
+		}
+		clearClassLoaderCaches(classLoader.getParent());
+	}
+
+}
diff --git a/spring-boot/src/main/resources/META-INF/spring.factories b/spring-boot/src/main/resources/META-INF/spring.factories
index aed00315ca0..da1d266b2f1 100644
--- a/spring-boot/src/main/resources/META-INF/spring.factories
+++ b/spring-boot/src/main/resources/META-INF/spring.factories
@@ -16,6 +16,7 @@ org.springframework.boot.context.web.ServerPortInfoApplicationContextInitializer
 
 # Application Listeners
 org.springframework.context.ApplicationListener=\
+org.springframework.boot.ClearCachesApplicationListener,\
 org.springframework.boot.builder.ParentContextCloserApplicationListener,\
 org.springframework.boot.context.FileEncodingApplicationListener,\
 org.springframework.boot.context.config.AnsiOutputApplicationListener,\