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 fb195d6c55f..e2b014f703a 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
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2020 the original author or authors.
+ * Copyright 2012-2021 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.
@@ -169,6 +169,7 @@ 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 fde52183670..fb77852da07 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
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2020 the original author or authors.
+ * Copyright 2012-2021 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.
@@ -165,6 +165,7 @@ 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 11f379fa5aa..779a30ebc7f 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
@@ -437,6 +437,30 @@ 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 965e63c3098..1807c310e6a 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
@@ -1119,6 +1119,31 @@ public abstract class AbstractServletWebServerFactoryTests {
 		}
 	}
 
+	@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);
 	}