diff --git a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/HateoasObjenesisCacheDisabler.java b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/HateoasObjenesisCacheDisabler.java
new file mode 100644
index 0000000000..eea57cfdc6
--- /dev/null
+++ b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/HateoasObjenesisCacheDisabler.java
@@ -0,0 +1,64 @@
+/*
+ * 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.devtools.autoconfigure;
+
+import java.lang.reflect.Field;
+
+import javax.annotation.PostConstruct;
+
+import org.springframework.objenesis.ObjenesisStd;
+import org.springframework.util.ClassUtils;
+import org.springframework.util.ReflectionUtils;
+
+/**
+ * Replaces the Objenesis instance in Spring HATEOAS's {@code DummyInvocationUtils} with
+ * one that does not perform any caching. The cache is problematic as it's keyed on class
+ * name which leads to {@code ClassCastExceptions} as the class loader changes across
+ * restarts.
+ *
+ * @author Andy Wilkinson
+ * @since 1.3.0
+ */
+class HateoasObjenesisCacheDisabler {
+
+	private static boolean cacheDisabled;
+
+	@PostConstruct
+	void disableCaching() {
+		if (!cacheDisabled) {
+			cacheDisabled = true;
+			doDisableCaching();
+		}
+	}
+
+	private void doDisableCaching() {
+		try {
+			Class<?> type = ClassUtils.forName(
+					"org.springframework.hateoas.core.DummyInvocationUtils",
+					getClass().getClassLoader());
+			Field objenesis = ReflectionUtils.findField(type, "OBJENESIS");
+			if (objenesis != null) {
+				ReflectionUtils.makeAccessible(objenesis);
+				ReflectionUtils.setField(objenesis, null, new ObjenesisStd(false));
+			}
+		}
+		catch (Exception ex) {
+			// Assume that Spring HATEOAS is not on the classpath and continue
+		}
+	}
+
+}
diff --git a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/LocalDevToolsAutoConfiguration.java b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/LocalDevToolsAutoConfiguration.java
index fd67a78460..2c916e6bbd 100644
--- a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/LocalDevToolsAutoConfiguration.java
+++ b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/LocalDevToolsAutoConfiguration.java
@@ -126,6 +126,11 @@ public class LocalDevToolsAutoConfiguration {
 					this.properties.getRestart().getAllExclude());
 		}
 
+		@Bean
+		public HateoasObjenesisCacheDisabler hateoasObjenesisCacheDisabler() {
+			return new HateoasObjenesisCacheDisabler();
+		}
+
 		@Bean
 		public FileSystemWatcherFactory fileSystemWatcherFactory() {
 			return new FileSystemWatcherFactory() {