diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyReactiveWebServerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyReactiveWebServerFactory.java
index b386bbaab0..531667de61 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyReactiveWebServerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyReactiveWebServerFactory.java
@@ -172,6 +172,7 @@ public class JettyReactiveWebServerFactory extends AbstractReactiveWebServerFact
 		InetSocketAddress address = new InetSocketAddress(getAddress(), port);
 		Server server = new Server(getThreadPool());
 		server.addConnector(createConnector(address, server));
+		server.setStopTimeout(0);
 		ServletHolder servletHolder = new ServletHolder(servlet);
 		servletHolder.setAsyncSupported(true);
 		ServletContextHandler contextHandler = new ServletContextHandler(server, "/", false, false);
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
index 2385cf663d..d53ef01a11 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyServletWebServerFactory.java
@@ -173,6 +173,7 @@ public class JettyServletWebServerFactory extends AbstractServletWebServerFactor
 	private Server createServer(InetSocketAddress address) {
 		Server server = new Server(getThreadPool());
 		server.setConnectors(new Connector[] { createConnector(address, server) });
+		server.setStopTimeout(0);
 		return server;
 	}
 
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/server/AbstractReactiveWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/server/AbstractReactiveWebServerFactoryTests.java
index 5f95b61c2b..f8ece0a60d 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/server/AbstractReactiveWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/reactive/server/AbstractReactiveWebServerFactoryTests.java
@@ -431,6 +431,30 @@ public abstract class AbstractReactiveWebServerFactoryTests {
 		blockingHandler.completeOne();
 	}
 
+	@Test
+	void whenARequestIsActiveAfterGracefulShutdownEndsThenStopWillComplete() throws InterruptedException {
+		AbstractReactiveWebServerFactory factory = getFactory();
+		factory.setShutdown(Shutdown.GRACEFUL);
+		BlockingHandler blockingHandler = new BlockingHandler();
+		this.webServer = factory.getWebServer(blockingHandler);
+		this.webServer.start();
+		Mono<ResponseEntity<Void>> request = getWebClient(this.webServer.getPort()).build().get().retrieve()
+				.toBodilessEntity();
+		AtomicReference<ResponseEntity<Void>> responseReference = new AtomicReference<>();
+		CountDownLatch responseLatch = new CountDownLatch(1);
+		request.subscribe((response) -> {
+			responseReference.set(response);
+			responseLatch.countDown();
+		});
+		blockingHandler.awaitQueue();
+		AtomicReference<GracefulShutdownResult> result = new AtomicReference<>();
+		this.webServer.shutDownGracefully(result::set);
+		this.webServer.stop();
+		Awaitility.await().atMost(Duration.ofSeconds(30))
+				.until(() -> GracefulShutdownResult.REQUESTS_ACTIVE == result.get());
+		blockingHandler.completeOne();
+	}
+
 	@Test
 	void whenARequestIsActiveThenStopWillComplete() throws InterruptedException, BrokenBarrierException {
 		AbstractReactiveWebServerFactory factory = getFactory();
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
index 9e1096101a..74bb1ad2e0 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/servlet/server/AbstractServletWebServerFactoryTests.java
@@ -1159,6 +1159,31 @@ public abstract class AbstractServletWebServerFactoryTests {
 		assertThat(getResponse("http://localhost:" + this.webServer.getPort() + "/hello")).isEqualTo("Hello World");
 	}
 
+	@Test
+	void whenARequestIsActiveAfterGracefulShutdownEndsThenStopWillComplete()
+			throws InterruptedException, BrokenBarrierException {
+		AbstractServletWebServerFactory factory = getFactory();
+		factory.setShutdown(Shutdown.GRACEFUL);
+		BlockingServlet blockingServlet = new BlockingServlet();
+		this.webServer = factory
+				.getWebServer((context) -> context.addServlet("blockingServlet", blockingServlet).addMapping("/"));
+		this.webServer.start();
+		int port = this.webServer.getPort();
+		initiateGetRequest(port, "/");
+		blockingServlet.awaitQueue();
+		AtomicReference<GracefulShutdownResult> result = new AtomicReference<>();
+		this.webServer.shutDownGracefully(result::set);
+		this.webServer.stop();
+		Awaitility.await().atMost(Duration.ofSeconds(30))
+				.until(() -> GracefulShutdownResult.REQUESTS_ACTIVE == result.get());
+		try {
+			blockingServlet.admitOne();
+		}
+		catch (RuntimeException ex) {
+
+		}
+	}
+
 	protected Future<Object> initiateGetRequest(int port, String path) {
 		return initiateGetRequest(HttpClients.createMinimal(), port, path);
 	}