diff --git a/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/jdt/ls/ClasspathListenerManager.java b/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/jdt/ls/ClasspathListenerManager.java
index 17b36692b..c60ba0126 100644
--- a/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/jdt/ls/ClasspathListenerManager.java
+++ b/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/jdt/ls/ClasspathListenerManager.java
@@ -84,11 +84,19 @@ public class ClasspathListenerManager {
 
 		// Cleanups:
 		return () -> {
-			unregisterCommand.dispose();
-			thenLog(log, this.server.getClient().removeClasspathListener(new ClasspathListenerParams(callbackCommandId)));
-			thenLog(log, this.server.getClient().unregisterCapability(new UnregistrationParams(ImmutableList.of(
-					new Unregistration(registrationId, WORKSPACE_EXECUTE_COMMAND)
-			))));
+			try {
+				log.info("Unregistering classpath callback "+callbackCommandId +" ...");
+				this.server.getClient().removeClasspathListener(
+						new ClasspathListenerParams(callbackCommandId)
+				).join();
+				log.info("Unregistering classpath callback "+callbackCommandId +" OK");
+				this.server.getClient().unregisterCapability(new UnregistrationParams(ImmutableList.of(
+						new Unregistration(registrationId, WORKSPACE_EXECUTE_COMMAND)
+				))).join();
+				unregisterCommand.dispose();
+			} catch (Exception e) {
+				log.error("", e);
+			}
 		};
 	}
 
diff --git a/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/util/SimpleLanguageServer.java b/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/util/SimpleLanguageServer.java
index 1f4ee4e31..85aa7186b 100644
--- a/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/util/SimpleLanguageServer.java
+++ b/headless-services/commons/commons-language-server/src/main/java/org/springframework/ide/vscode/commons/languageserver/util/SimpleLanguageServer.java
@@ -432,12 +432,14 @@ public class SimpleLanguageServer implements Sts4LanguageServer, LanguageClientA
 
 	@Override
 	public CompletableFuture<Object> shutdown() {
+	  return async.invoke(() -> {
 		Runnable h = shutdownHandler;
 		if (h!=null) {
 			h.run();
 		}
 		getWorkspaceService().dispose();
-		return CompletableFuture.completedFuture(new Object());
+		return "OK";
+	  });
 	}
 
 	@Override
diff --git a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JdtLsProjectCache.java b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JdtLsProjectCache.java
index a631258b4..f9a5c2a6c 100644
--- a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JdtLsProjectCache.java
+++ b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JdtLsProjectCache.java
@@ -76,7 +76,7 @@ public class JdtLsProjectCache implements JavaProjectFinder, ProjectObserver {
 			}))
 		);
 		this.server.onShutdown(() -> 
-			disposable.thenAccept(Disposable::dispose)
+			disposable.thenAccept(Disposable::dispose).join()
 		);
 	}
 
diff --git a/vscode-extensions/commons-vscode/src/classpath.ts b/vscode-extensions/commons-vscode/src/classpath.ts
index 95ac14c64..4910c66bd 100644
--- a/vscode-extensions/commons-vscode/src/classpath.ts
+++ b/vscode-extensions/commons-vscode/src/classpath.ts
@@ -6,10 +6,16 @@ import { LanguageClient, RequestType } from 'vscode-languageclient';
 
 export function registerClasspathService(client : LanguageClient) : void {
 
-    let classpathListenerRequest = new RequestType<ClasspathListenerParams, ClasspathListenerResponse, void, void>("sts/addClasspathListener");
-    client.onRequest(classpathListenerRequest, async (params: ClasspathListenerParams) => {
+    let addRequest = new RequestType<ClasspathListenerParams, ClasspathListenerResponse, void, void>("sts/addClasspathListener");
+    client.onRequest(addRequest, async (params: ClasspathListenerParams) => {
         return <ClasspathListenerResponse> await VSCode.commands.executeCommand("java.execute.workspaceCommand", "sts.java.addClasspathListener", params.callbackCommandId);
     });
+
+    let removeRequest = new RequestType<ClasspathListenerParams, ClasspathListenerResponse, void, void>("sts/removeClasspathListener");
+    client.onRequest(removeRequest, async (params: ClasspathListenerParams) => {
+        return <ClasspathListenerResponse> await VSCode.commands.executeCommand("java.execute.workspaceCommand", "sts.java.removeClasspathListener", params.callbackCommandId);
+    });
+
 }
 
 interface ClasspathListenerParams {
diff --git a/vscode-extensions/vscode-spring-boot/lib/Main.ts b/vscode-extensions/vscode-spring-boot/lib/Main.ts
index 6673402a2..07de35d22 100644
--- a/vscode-extensions/vscode-spring-boot/lib/Main.ts
+++ b/vscode-extensions/vscode-spring-boot/lib/Main.ts
@@ -20,7 +20,7 @@ const JAVA_LANGUAGE_ID = "java";
 export function activate(context: VSCode.ExtensionContext) {
     let options : commons.ActivatorOptions = {
         DEBUG: false,
-        CONNECT_TO_LS: false,
+        CONNECT_TO_LS: true,
         extensionId: 'vscode-spring-boot',
         preferJdk: true,
         checkjvm: (context: VSCode.ExtensionContext, jvm: commons.JVM) => {