diff --git a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploader.java b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploader.java
index 091c0e022135..44f714182bb0 100644
--- a/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploader.java
+++ b/spring-boot-project/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploader.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2018 the original author or authors.
+ * Copyright 2012-2019 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.
@@ -19,8 +19,8 @@
 import java.io.ByteArrayOutputStream;
 import java.io.IOException;
 import java.io.ObjectOutputStream;
-import java.net.ConnectException;
 import java.net.MalformedURLException;
+import java.net.SocketException;
 import java.net.URI;
 import java.net.URISyntaxException;
 import java.net.URL;
@@ -117,9 +117,10 @@ private void performUpload(ClassLoaderFiles classLoaderFiles, byte[] bytes)
 					logUpload(classLoaderFiles);
 					return;
 				}
-				catch (ConnectException ex) {
-					logger.warn("Failed to connect when uploading to " + this.uri
+				catch (SocketException ex) {
+					logger.warn("A failure occurred when uploading to " + this.uri
 							+ ". Upload will be retried in 2 seconds");
+					logger.debug("Upload failure", ex);
 					Thread.sleep(2000);
 				}
 			}
diff --git a/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploaderTests.java b/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploaderTests.java
index 05fed152147c..5a637a8ecebb 100644
--- a/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploaderTests.java
+++ b/spring-boot-project/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/remote/client/ClassPathChangeUploaderTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2018 the original author or authors.
+ * Copyright 2012-2019 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.
@@ -20,7 +20,7 @@
 import java.io.File;
 import java.io.IOException;
 import java.io.ObjectInputStream;
-import java.net.ConnectException;
+import java.net.SocketException;
 import java.util.Collection;
 import java.util.Iterator;
 import java.util.LinkedHashSet;
@@ -111,10 +111,10 @@ public void sendsClassLoaderFiles() throws Exception {
 	}
 
 	@Test
-	public void retriesOnConnectException() throws Exception {
+	public void retriesOnSocketException() throws Exception {
 		File sourceFolder = this.temp.newFolder();
 		ClassPathChangedEvent event = createClassPathChangedEvent(sourceFolder);
-		this.requestFactory.willRespond(new ConnectException());
+		this.requestFactory.willRespond(new SocketException());
 		this.requestFactory.willRespond(HttpStatus.OK);
 		this.uploader.onApplicationEvent(event);
 		assertThat(this.requestFactory.getExecutedRequests()).hasSize(2);