diff --git a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ClassLoaderFilesResourcePatternResolver.java b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ClassLoaderFilesResourcePatternResolver.java
index 37d8d07809b..3deed7db9f3 100644
--- a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ClassLoaderFilesResourcePatternResolver.java
+++ b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/restart/ClassLoaderFilesResourcePatternResolver.java
@@ -130,7 +130,7 @@ final class ClassLoaderFilesResourcePatternResolver implements ResourcePatternRe
 			for (Entry<String, ClassLoaderFile> entry : sourceFolder.getFilesEntrySet()) {
 				String name = entry.getKey();
 				ClassLoaderFile file = entry.getValue();
-				if (file.getKind() == Kind.ADDED
+				if (entry.getValue().getKind() != Kind.DELETED
 						&& this.antPathMatcher.match(trimmedLocationPattern, name)) {
 					URL url = new URL("reloaded", null, -1, "/" + name,
 							new ClassLoaderFileURLStreamHandler(file));
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-devtools-tests/src/test/java/org/springframework/boot/devtools/tests/DevToolsIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-devtools-tests/src/test/java/org/springframework/boot/devtools/tests/DevToolsIntegrationTests.java
index 9d3afa749c3..9a141dd7e09 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-devtools-tests/src/test/java/org/springframework/boot/devtools/tests/DevToolsIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-devtools-tests/src/test/java/org/springframework/boot/devtools/tests/DevToolsIntegrationTests.java
@@ -125,6 +125,53 @@ public class DevToolsIntegrationTests {
 
 	}
 
+	@Test
+	public void createAControllerAndThenAddARequestMapping() throws Exception {
+		TestRestTemplate template = new TestRestTemplate();
+		String urlBase = "http://localhost:" + awaitServerPort();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForEntity(urlBase + "/two", String.class).getStatusCode())
+				.isEqualTo(HttpStatus.NOT_FOUND);
+		controller("com.example.ControllerTwo").withRequestMapping("two").build();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForObject("http://localhost:" + awaitServerPort() + "/two",
+				String.class)).isEqualTo("two");
+		controller("com.example.ControllerTwo").withRequestMapping("two")
+				.withRequestMapping("three").build();
+		assertThat(template.getForObject(
+				"http://localhost:" + awaitServerPort() + "/three", String.class))
+						.isEqualTo("three");
+	}
+
+	@Test
+	public void createAControllerAndThenAddARequestMappingToAnExistingController()
+			throws Exception {
+		TestRestTemplate template = new TestRestTemplate();
+		String urlBase = "http://localhost:" + awaitServerPort();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForEntity(urlBase + "/two", String.class).getStatusCode())
+				.isEqualTo(HttpStatus.NOT_FOUND);
+		controller("com.example.ControllerTwo").withRequestMapping("two").build();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForObject("http://localhost:" + awaitServerPort() + "/two",
+				String.class)).isEqualTo("two");
+		controller("com.example.ControllerOne").withRequestMapping("one")
+				.withRequestMapping("three").build();
+		int port = awaitServerPort();
+		assertThat(
+				template.getForObject("http://localhost:" + port + "/one", String.class))
+						.isEqualTo("one");
+		assertThat(
+				template.getForObject("http://localhost:" + port + "/two", String.class))
+						.isEqualTo("two");
+		assertThat(template.getForObject("http://localhost:" + port + "/three",
+				String.class)).isEqualTo("three");
+	}
+
 	@Test
 	public void deleteAController() throws Exception {
 		TestRestTemplate template = new TestRestTemplate();
@@ -137,6 +184,25 @@ public class DevToolsIntegrationTests {
 
 	}
 
+	@Test
+	public void createAControllerAndThenDeleteIt() throws Exception {
+		TestRestTemplate template = new TestRestTemplate();
+		String urlBase = "http://localhost:" + awaitServerPort();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForEntity(urlBase + "/two", String.class).getStatusCode())
+				.isEqualTo(HttpStatus.NOT_FOUND);
+		controller("com.example.ControllerTwo").withRequestMapping("two").build();
+		assertThat(template.getForObject(urlBase + "/one", String.class))
+				.isEqualTo("one");
+		assertThat(template.getForObject("http://localhost:" + awaitServerPort() + "/two",
+				String.class)).isEqualTo("two");
+		assertThat(new File(this.launchedApplication.getClassesDirectory(),
+				"com/example/ControllerTwo.class").delete()).isTrue();
+		assertThat(template.getForEntity("http://localhost:" + awaitServerPort() + "/two",
+				String.class).getStatusCode()).isEqualTo(HttpStatus.NOT_FOUND);
+	}
+
 	private int awaitServerPort() throws Exception {
 		long end = System.currentTimeMillis() + 30000;
 		while (this.serverPortFile.length() == 0) {