diff --git a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ChangeableUrls.java b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ChangeableUrls.java
index da8434b962..9356c4cb4e 100644
--- a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ChangeableUrls.java
+++ b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ChangeableUrls.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2015 the original author or authors.
+ * Copyright 2012-2016 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.
@@ -16,6 +16,9 @@
 
 package org.springframework.boot.devtools.restart;
 
+import java.io.File;
+import java.io.IOException;
+import java.net.MalformedURLException;
 import java.net.URL;
 import java.net.URLClassLoader;
 import java.util.ArrayList;
@@ -23,13 +26,18 @@ import java.util.Collection;
 import java.util.Collections;
 import java.util.Iterator;
 import java.util.List;
+import java.util.jar.Attributes;
+import java.util.jar.JarFile;
+import java.util.jar.Manifest;
 
 import org.springframework.boot.devtools.settings.DevToolsSettings;
+import org.springframework.util.StringUtils;
 
 /**
- * A filtered collections of URLs which can be change after the application has started.
+ * A filtered collection of URLs which can change after the application has started.
  *
  * @author Phillip Webb
+ * @author Andy Wilkinson
  */
 final class ChangeableUrls implements Iterable<URL> {
 
@@ -74,7 +82,59 @@ final class ChangeableUrls implements Iterable<URL> {
 	}
 
 	public static ChangeableUrls fromUrlClassLoader(URLClassLoader classLoader) {
-		return fromUrls(classLoader.getURLs());
+		List<URL> urls = new ArrayList<URL>();
+		for (URL url : classLoader.getURLs()) {
+			urls.add(url);
+			urls.addAll(getUrlsFromClassPathOfJarManifestIfPossible(url));
+		}
+		return fromUrls(urls);
+	}
+
+	private static List<URL> getUrlsFromClassPathOfJarManifestIfPossible(URL url) {
+		JarFile jarFile = getJarFileIfPossible(url);
+		if (jarFile != null) {
+			try {
+				return getUrlsFromClassPathAttribute(jarFile.getManifest());
+			}
+			catch (IOException ex) {
+				throw new IllegalStateException(
+						"Failed to read Class-Path attribute from manifest of jar "
+								+ url);
+			}
+		}
+		return Collections.<URL>emptyList();
+	}
+
+	private static JarFile getJarFileIfPossible(URL url) {
+		try {
+			File file = new File(url.toURI());
+			if (file.isFile()) {
+				return new JarFile(file);
+			}
+		}
+		catch (Exception ex) {
+			// Assume it's not a jar and continue
+		}
+		return null;
+	}
+
+	private static List<URL> getUrlsFromClassPathAttribute(Manifest manifest) {
+		List<URL> urls = new ArrayList<URL>();
+		String classPathAttribute = manifest.getMainAttributes()
+				.getValue(Attributes.Name.CLASS_PATH);
+		if (StringUtils.hasText(classPathAttribute)) {
+			for (String entry : StringUtils.delimitedListToStringArray(classPathAttribute,
+					" ")) {
+				try {
+					urls.add(new URL(entry));
+				}
+				catch (MalformedURLException ex) {
+					throw new IllegalStateException(
+							"Class-Path attribute contains malformed URL", ex);
+				}
+			}
+		}
+		return urls;
 	}
 
 	public static ChangeableUrls fromUrls(Collection<URL> urls) {
diff --git a/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/restart/ChangeableUrlsTests.java b/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/restart/ChangeableUrlsTests.java
index efcde69446..723e558866 100644
--- a/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/restart/ChangeableUrlsTests.java
+++ b/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/restart/ChangeableUrlsTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2015 the original author or authors.
+ * Copyright 2012-2016 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.
@@ -17,13 +17,21 @@
 package org.springframework.boot.devtools.restart;
 
 import java.io.File;
+import java.io.FileOutputStream;
 import java.io.IOException;
 import java.net.URL;
+import java.net.URLClassLoader;
+import java.util.jar.Attributes;
+import java.util.jar.JarOutputStream;
+import java.util.jar.Manifest;
 
 import org.junit.Rule;
 import org.junit.Test;
 import org.junit.rules.TemporaryFolder;
 
+import org.springframework.util.StringUtils;
+
+import static org.hamcrest.Matchers.contains;
 import static org.hamcrest.Matchers.equalTo;
 import static org.junit.Assert.assertThat;
 
@@ -31,6 +39,7 @@ import static org.junit.Assert.assertThat;
  * Tests for {@link ChangeableUrls}.
  *
  * @author Phillip Webb
+ * @author Andy Wilkinson
  */
 public class ChangeableUrlsTests {
 
@@ -64,6 +73,16 @@ public class ChangeableUrlsTests {
 		assertThat(urls.size(), equalTo(0));
 	}
 
+	@Test
+	public void urlsFromJarClassPathAreConsidered() throws Exception {
+		URL projectCore = makeUrl("project-core");
+		URL projectWeb = makeUrl("project-web");
+		ChangeableUrls urls = ChangeableUrls.fromUrlClassLoader(new URLClassLoader(
+				new URL[] { makeJarFileWithUrlsInManifestClassPath(projectCore,
+						projectWeb) }));
+		assertThat(urls.toList(), contains(projectCore, projectWeb));
+	}
+
 	private URL makeUrl(String name) throws IOException {
 		File file = this.temporaryFolder.newFolder();
 		file = new File(file, name);
@@ -73,4 +92,15 @@ public class ChangeableUrlsTests {
 		return file.toURI().toURL();
 	}
 
+	private URL makeJarFileWithUrlsInManifestClassPath(URL... urls) throws Exception {
+		File classpathJar = this.temporaryFolder.newFile("classpath.jar");
+		Manifest manifest = new Manifest();
+		manifest.getMainAttributes().putValue(Attributes.Name.MANIFEST_VERSION.toString(),
+				"1.0");
+		manifest.getMainAttributes().putValue(Attributes.Name.CLASS_PATH.toString(),
+				StringUtils.arrayToDelimitedString(urls, " "));
+		new JarOutputStream(new FileOutputStream(classpathJar), manifest).close();
+		return classpathJar.toURI().toURL();
+	}
+
 }