diff --git a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JavaProjectsServiceWithFallback.java b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JavaProjectsServiceWithFallback.java
index a976b9d41..d15351cac 100644
--- a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JavaProjectsServiceWithFallback.java
+++ b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/jdt/ls/JavaProjectsServiceWithFallback.java
@@ -31,6 +31,7 @@ import com.google.common.base.Suppliers;
 import com.google.common.collect.ImmutableList;
 
 import reactor.core.Disposable;
+import reactor.core.publisher.Mono;
 
 public class JavaProjectsServiceWithFallback implements JavaProjectsService {
 
@@ -80,7 +81,9 @@ public class JavaProjectsServiceWithFallback implements JavaProjectsService {
 
 		this.mainServiceInitialized = this.server
 				.onInitialized(main.initialize())
-				.timeout(Duration.ofSeconds(5))
+				.doOnError(error -> {
+					log.warn("JDT-based JavaProject service not available, will use fallback service", error);
+				})
 				.toFuture();
 
 		this.server.onShutdown(() -> {
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 a77c4b5c2..f419f68d5 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
@@ -16,6 +16,7 @@ import java.net.URI;
 import java.net.URISyntaxException;
 import java.net.URL;
 import java.net.URLDecoder;
+import java.time.Duration;
 import java.util.ArrayList;
 import java.util.Collection;
 import java.util.HashMap;
@@ -214,7 +215,7 @@ public class JdtLsProjectCache implements InitializableJavaProjectsService {
 
 	@Override
 	public Mono<Disposable> initialize() {
-		return server.addClasspathListener(new ClasspathListener() {
+		return Mono.defer(() -> server.addClasspathListener(new ClasspathListener() {
 			@Override
 			public void changed(Event event) {
 				log.debug("claspath event received {}", event);
@@ -254,7 +255,9 @@ public class JdtLsProjectCache implements InitializableJavaProjectsService {
 					}
 				});
 			}
-		}).doOnError(t -> {
+		})
+		.timeout(Duration.ofSeconds(5))
+		.doOnError(t -> {
 			if (isNoJdtError(t)) {
 				log.info("JDT Language Server not available. Fallback classpath provider will be used instead.");
 			} else if (isOldJdt(t)) {
@@ -262,7 +265,7 @@ public class JdtLsProjectCache implements InitializableJavaProjectsService {
 			} else {
 				log.error("Unexpected error registering classpath listener with JDT. Fallback classpath provider will be used instead.", t);
 			}
-		});
+		}));
 	}
 
 	@Override