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 74bb1ad2e05..d45071c2536 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
@@ -44,11 +44,11 @@ import java.util.EnumSet;
 import java.util.HashMap;
 import java.util.Locale;
 import java.util.Map;
+import java.util.Objects;
 import java.util.concurrent.ArrayBlockingQueue;
 import java.util.concurrent.BlockingQueue;
 import java.util.concurrent.BrokenBarrierException;
 import java.util.concurrent.Callable;
-import java.util.concurrent.CyclicBarrier;
 import java.util.concurrent.ExecutionException;
 import java.util.concurrent.Future;
 import java.util.concurrent.FutureTask;
@@ -1174,8 +1174,8 @@ public abstract class AbstractServletWebServerFactoryTests {
 		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());
+		assertThat(Awaitility.await().atMost(Duration.ofSeconds(30)).until(result::get, Objects::nonNull))
+				.isEqualTo(GracefulShutdownResult.REQUESTS_ACTIVE);
 		try {
 			blockingServlet.admitOne();
 		}
@@ -1524,7 +1524,7 @@ public abstract class AbstractServletWebServerFactoryTests {
 
 	protected static class BlockingServlet extends HttpServlet {
 
-		private final BlockingQueue<CyclicBarrier> barriers = new ArrayBlockingQueue<>(10);
+		private final BlockingQueue<Blocker> blockers = new ArrayBlockingQueue<>(10);
 
 		public BlockingServlet() {
 
@@ -1532,42 +1532,23 @@ public abstract class AbstractServletWebServerFactoryTests {
 
 		@Override
 		protected void doGet(HttpServletRequest req, HttpServletResponse resp) throws ServletException, IOException {
-			CyclicBarrier barrier = new CyclicBarrier(2);
-			this.barriers.add(barrier);
-			try {
-				barrier.await();
-			}
-			catch (InterruptedException ex) {
-				Thread.currentThread().interrupt();
-			}
-			catch (BrokenBarrierException ex) {
-				throw new ServletException(ex);
-			}
+			Blocker blocker = new Blocker();
+			this.blockers.add(blocker);
+			blocker.await();
 		}
 
-		public void admitOne() {
-			try {
-				CyclicBarrier barrier = this.barriers.take();
-				if (!barrier.isBroken()) {
-					barrier.await();
-				}
-			}
-			catch (InterruptedException ex) {
-				Thread.currentThread().interrupt();
-			}
-			catch (BrokenBarrierException ex) {
-				throw new RuntimeException(ex);
-			}
+		public void admitOne() throws InterruptedException {
+			this.blockers.take().clear();
 		}
 
 		public void awaitQueue() throws InterruptedException {
-			while (this.barriers.isEmpty()) {
+			while (this.blockers.isEmpty()) {
 				Thread.sleep(100);
 			}
 		}
 
 		public void awaitQueue(int size) throws InterruptedException {
-			while (this.barriers.size() < size) {
+			while (this.blockers.size() < size) {
 				Thread.sleep(100);
 			}
 		}
@@ -1576,45 +1557,58 @@ public abstract class AbstractServletWebServerFactoryTests {
 
 	static class BlockingAsyncServlet extends HttpServlet {
 
-		private final BlockingQueue<CyclicBarrier> barriers = new ArrayBlockingQueue<>(10);
+		private final BlockingQueue<Blocker> blockers = new ArrayBlockingQueue<>(10);
 
 		@Override
 		protected void doGet(HttpServletRequest req, HttpServletResponse resp) throws ServletException, IOException {
-			CyclicBarrier barrier = new CyclicBarrier(2);
-			this.barriers.add(barrier);
+			Blocker blocker = new Blocker();
+			this.blockers.add(blocker);
 			AsyncContext async = req.startAsync();
 			new Thread(() -> {
-				try {
-					barrier.await();
-				}
-				catch (InterruptedException ex) {
-					Thread.currentThread().interrupt();
-				}
-				catch (BrokenBarrierException ex) {
-
-				}
+				blocker.await();
 				async.complete();
 			}).start();
 		}
 
-		private void admitOne() {
-			try {
-				this.barriers.take().await();
-			}
-			catch (InterruptedException ex) {
-				Thread.currentThread().interrupt();
-			}
-			catch (BrokenBarrierException ex) {
-				throw new RuntimeException(ex);
-			}
+		private void admitOne() throws InterruptedException {
+			this.blockers.take().clear();
 		}
 
 		private void awaitQueue() throws InterruptedException {
-			while (this.barriers.isEmpty()) {
+			while (this.blockers.isEmpty()) {
 				Thread.sleep(100);
 			}
 		}
 
 	}
 
+	private static final class Blocker {
+
+		private boolean block = true;
+
+		private final Object monitor = new Object();
+
+		private void await() {
+			synchronized (this.monitor) {
+				while (this.block) {
+					try {
+						this.monitor.wait();
+					}
+					catch (InterruptedException ex) {
+						System.out.println("Interrupted!");
+						// Keep waiting
+					}
+				}
+			}
+		}
+
+		private void clear() {
+			synchronized (this.monitor) {
+				this.block = false;
+				this.monitor.notifyAll();
+			}
+		}
+
+	}
+
 }