diff --git a/gradle.properties b/gradle.properties
index a4a71dd5f4b..fbef36ce468 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -13,6 +13,6 @@ kotlinVersion=1.9.22
 mavenVersion=3.9.4
 nativeBuildToolsVersion=0.10.1
 springFrameworkVersion=6.1.4
-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 5d2209aad90..2accad1852a 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
@@ -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 +52,44 @@ 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();
+		CountDownLatch shutdownUnderway = new CountDownLatch(1);
+		new Thread(() -> doShutdown(callback, shutdownUnderway), "tomcat-shutdown").start();
+		try {
+			shutdownUnderway.await();
+		}
+		catch (InterruptedException ex) {
+			Thread.currentThread().interrupt();
+		}
 	}
 
-	private void doShutdown(GracefulShutdownCallback callback) {
-		List<Connector> connectors = getConnectors();
-		connectors.forEach(this::close);
+	private void doShutdown(GracefulShutdownCallback callback, CountDownLatch shutdownUnderway) {
 		try {
-			for (Container host : this.tomcat.getEngine().findChildren()) {
-				for (Container context : host.findChildren()) {
-					while (!this.aborted && isActive(context)) {
-						Thread.sleep(50);
-					}
-					if (this.aborted) {
-						logger.info("Graceful shutdown aborted with one or more requests still active");
-						callback.shutdownComplete(GracefulShutdownResult.REQUESTS_ACTIVE);
-						return;
+			List<Connector> connectors = getConnectors();
+			connectors.forEach(this::close);
+			shutdownUnderway.countDown();
+			try {
+				for (Container host : this.tomcat.getEngine().findChildren()) {
+					for (Container context : host.findChildren()) {
+						while (!this.aborted && isActive(context)) {
+							Thread.sleep(50);
+						}
+						if (this.aborted) {
+							logger.info("Graceful shutdown aborted with one or more requests still active");
+							callback.shutdownComplete(GracefulShutdownResult.REQUESTS_ACTIVE);
+							return;
+						}
 					}
 				}
 			}
-
+			catch (InterruptedException ex) {
+				Thread.currentThread().interrupt();
+			}
+			logger.info("Graceful shutdown complete");
+			callback.shutdownComplete(GracefulShutdownResult.IDLE);
 		}
-		catch (InterruptedException ex) {
-			Thread.currentThread().interrupt();
+		finally {
+			shutdownUnderway.countDown();
 		}
-		logger.info("Graceful shutdown complete");
-		callback.shutdownComplete(GracefulShutdownResult.IDLE);
 	}
 
 	private List<Connector> getConnectors() {