diff --git a/gradle.properties b/gradle.properties
index acf983594f..0183c8f5fb 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -13,6 +13,6 @@ kotlinVersion=1.8.22
 mavenVersion=3.9.4
 nativeBuildToolsVersion=0.9.28
 springFrameworkVersion=6.0.17
-tomcatVersion=10.1.18
+tomcatVersion=10.1.19
 
 kotlin.stdlib.default.dependency=false
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/GracefulShutdown.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/GracefulShutdown.java
index c921cf5c94..b94f92c6d3 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/GracefulShutdown.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/GracefulShutdown.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2020 the original author or authors.
+ * Copyright 2012-2024 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.
@@ -19,6 +19,7 @@ package org.springframework.boot.web.embedded.tomcat;
 import java.util.ArrayList;
 import java.util.Collections;
 import java.util.List;
+import java.util.concurrent.CountDownLatch;
 
 import org.apache.catalina.Container;
 import org.apache.catalina.Service;
@@ -51,32 +52,45 @@ final class GracefulShutdown {
 
 	void shutDownGracefully(GracefulShutdownCallback callback) {
 		logger.info("Commencing graceful shutdown. Waiting for active requests to complete");
-		new Thread(() -> doShutdown(callback), "tomcat-shutdown").start();
-	}
-
-	private void doShutdown(GracefulShutdownCallback callback) {
-		List<Connector> connectors = getConnectors();
-		connectors.forEach(this::close);
+		CountDownLatch shutdownUnderway = new CountDownLatch(1);
+		new Thread(() -> doShutdown(callback, shutdownUnderway), "tomcat-shutdown").start();
 		try {
-			for (Container host : this.tomcat.getEngine().findChildren()) {
-				for (Container context : host.findChildren()) {
-					while (isActive(context)) {
-						if (this.aborted) {
-							logger.info("Graceful shutdown aborted with one or more requests still active");
-							callback.shutdownComplete(GracefulShutdownResult.REQUESTS_ACTIVE);
-							return;
-						}
-						Thread.sleep(50);
-					}
-				}
-			}
-
+			shutdownUnderway.await();
 		}
 		catch (InterruptedException ex) {
 			Thread.currentThread().interrupt();
 		}
-		logger.info("Graceful shutdown complete");
-		callback.shutdownComplete(GracefulShutdownResult.IDLE);
+	}
+
+	private void doShutdown(GracefulShutdownCallback callback, CountDownLatch shutdownUnderway) {
+		try {
+			List<Connector> connectors = getConnectors();
+			connectors.forEach(this::close);
+			shutdownUnderway.countDown();
+			try {
+				for (Container host : this.tomcat.getEngine().findChildren()) {
+					for (Container context : host.findChildren()) {
+						while (isActive(context)) {
+							if (this.aborted) {
+								logger.info("Graceful shutdown aborted with one or more requests still active");
+								callback.shutdownComplete(GracefulShutdownResult.REQUESTS_ACTIVE);
+								return;
+							}
+							Thread.sleep(50);
+						}
+					}
+				}
+
+			}
+			catch (InterruptedException ex) {
+				Thread.currentThread().interrupt();
+			}
+			logger.info("Graceful shutdown complete");
+			callback.shutdownComplete(GracefulShutdownResult.IDLE);
+		}
+		finally {
+			shutdownUnderway.countDown();
+		}
 	}
 
 	private List<Connector> getConnectors() {