diff --git a/module/spring-boot-web-server-test/src/test/java/org/springframework/boot/web/server/test/client/reactive/WebTestClientContextCustomizerTcfCacheContextPausingTests.java b/module/spring-boot-web-server-test/src/test/java/org/springframework/boot/web/server/test/client/reactive/WebTestClientContextCustomizerTcfCacheContextPausingTests.java
new file mode 100644
index 00000000000..adbdad6854b
--- /dev/null
+++ b/module/spring-boot-web-server-test/src/test/java/org/springframework/boot/web/server/test/client/reactive/WebTestClientContextCustomizerTcfCacheContextPausingTests.java
@@ -0,0 +1,125 @@
+/*
+ * Copyright 2012-present 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.web.server.test.client.reactive;
+
+import java.util.Collections;
+import java.util.Map;
+
+import org.junit.jupiter.api.Nested;
+import org.junit.jupiter.api.Test;
+import reactor.core.publisher.Mono;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.SpringBootConfiguration;
+import org.springframework.boot.test.context.SpringBootTest;
+import org.springframework.boot.tomcat.reactive.TomcatReactiveWebServerFactory;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Import;
+import org.springframework.core.io.buffer.DefaultDataBufferFactory;
+import org.springframework.http.HttpStatus;
+import org.springframework.http.server.reactive.ContextPathCompositeHandler;
+import org.springframework.http.server.reactive.HttpHandler;
+import org.springframework.http.server.reactive.ServerHttpRequest;
+import org.springframework.http.server.reactive.ServerHttpResponse;
+import org.springframework.test.context.TestPropertySource;
+import org.springframework.test.web.reactive.server.WebTestClient;
+
+/**
+ * Tests for {@link WebTestClientContextCustomizer} when the test context framework pauses
+ * a context while it's in the cache.
+ *
+ * @author Andy Wilkinson
+ */
+@SpringBootTest(webEnvironment = SpringBootTest.WebEnvironment.RANDOM_PORT,
+		properties = "spring.main.web-application-type=none")
+class WebTestClientContextCustomizerTcfCacheContextPausingTests {
+
+	@Nested
+	@Import(TestConfig.class)
+	@TestPropertySource(properties = { "context=one", "spring.main.web-application-type=reactive" })
+	class ContextOne {
+
+		@Autowired
+		private WebTestClient webTestClient;
+
+		@Test
+		void test() {
+			this.webTestClient.get().uri("/test").exchange().expectBody(String.class).isEqualTo("hello world");
+		}
+
+	}
+
+	@Nested
+	@Import(TestConfig.class)
+	@TestPropertySource(properties = { "context=two", "spring.main.web-application-type=reactive" })
+	class ContextTwo {
+
+		@Autowired
+		private WebTestClient webTestClient;
+
+		@Test
+		void test() {
+			this.webTestClient.get().uri("/test").exchange().expectBody(String.class).isEqualTo("hello world");
+		}
+
+	}
+
+	@Nested
+	@Import(TestConfig.class)
+	@TestPropertySource(properties = { "context=one", "spring.main.web-application-type=reactive" })
+	class ReuseContextOne {
+
+		@Autowired
+		private WebTestClient webTestClient;
+
+		@Test
+		void test() {
+			this.webTestClient.get().uri("/test").exchange().expectBody(String.class).isEqualTo("hello world");
+		}
+
+	}
+
+	@SpringBootConfiguration(proxyBeanMethods = false)
+	static class TestConfig {
+
+		@Bean
+		TomcatReactiveWebServerFactory webServerFactory() {
+			return new TomcatReactiveWebServerFactory(0);
+		}
+
+		@Bean
+		HttpHandler httpHandler() {
+			TestHandler httpHandler = new TestHandler();
+			Map<String, HttpHandler> handlersMap = Collections.singletonMap("/test", httpHandler);
+			return new ContextPathCompositeHandler(handlersMap);
+		}
+
+	}
+
+	static class TestHandler implements HttpHandler {
+
+		private static final DefaultDataBufferFactory factory = new DefaultDataBufferFactory();
+
+		@Override
+		public Mono<Void> handle(ServerHttpRequest request, ServerHttpResponse response) {
+			response.setStatusCode(HttpStatus.OK);
+			return response.writeWith(Mono.just(factory.wrap("hello world".getBytes())));
+		}
+
+	}
+
+}
diff --git a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/context/WebServerGracefulShutdownLifecycle.java b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/context/WebServerGracefulShutdownLifecycle.java
index 8091615a932..682c329c541 100644
--- a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/context/WebServerGracefulShutdownLifecycle.java
+++ b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/context/WebServerGracefulShutdownLifecycle.java
@@ -75,4 +75,9 @@ public final class WebServerGracefulShutdownLifecycle implements SmartLifecycle
 		return WebServerApplicationContext.GRACEFUL_SHUTDOWN_PHASE;
 	}
 
+	@Override
+	public boolean isPauseable() {
+		return false;
+	}
+
 }
diff --git a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/reactive/context/WebServerStartStopLifecycle.java b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/reactive/context/WebServerStartStopLifecycle.java
index 097117d6c31..331e0d6db6c 100644
--- a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/reactive/context/WebServerStartStopLifecycle.java
+++ b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/reactive/context/WebServerStartStopLifecycle.java
@@ -58,4 +58,9 @@ class WebServerStartStopLifecycle implements SmartLifecycle {
 		return WebServerApplicationContext.START_STOP_LIFECYCLE_PHASE;
 	}
 
+	@Override
+	public boolean isPauseable() {
+		return false;
+	}
+
 }
diff --git a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/servlet/context/WebServerStartStopLifecycle.java b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/servlet/context/WebServerStartStopLifecycle.java
index 131e7e822de..e84462026d4 100644
--- a/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/servlet/context/WebServerStartStopLifecycle.java
+++ b/module/spring-boot-web-server/src/main/java/org/springframework/boot/web/server/servlet/context/WebServerStartStopLifecycle.java
@@ -63,4 +63,9 @@ class WebServerStartStopLifecycle implements SmartLifecycle {
 		return WebServerApplicationContext.START_STOP_LIFECYCLE_PHASE;
 	}
 
+	@Override
+	public boolean isPauseable() {
+		return false;
+	}
+
 }