diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/server/ChildManagementContextInitializer.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/server/ChildManagementContextInitializer.java
index 38a6a68f36..579e7d7126 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/server/ChildManagementContextInitializer.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/server/ChildManagementContextInitializer.java
@@ -33,12 +33,13 @@ import org.springframework.boot.actuate.autoconfigure.web.ManagementContextFacto
 import org.springframework.boot.autoconfigure.context.PropertyPlaceholderAutoConfiguration;
 import org.springframework.boot.context.event.ApplicationFailedEvent;
 import org.springframework.boot.web.context.ConfigurableWebServerApplicationContext;
-import org.springframework.boot.web.context.WebServerInitializedEvent;
+import org.springframework.boot.web.context.WebServerGracefulShutdownLifecycle;
 import org.springframework.context.ApplicationContext;
 import org.springframework.context.ApplicationContextInitializer;
 import org.springframework.context.ApplicationEvent;
 import org.springframework.context.ApplicationListener;
 import org.springframework.context.ConfigurableApplicationContext;
+import org.springframework.context.SmartLifecycle;
 import org.springframework.context.annotation.AnnotationConfigRegistry;
 import org.springframework.context.aot.ApplicationContextAotGenerator;
 import org.springframework.context.event.ContextClosedEvent;
@@ -55,8 +56,7 @@ import org.springframework.util.Assert;
  * @author Andy Wilkinson
  * @author Phillip Webb
  */
-class ChildManagementContextInitializer
-		implements ApplicationListener<WebServerInitializedEvent>, BeanRegistrationAotProcessor {
+class ChildManagementContextInitializer implements BeanRegistrationAotProcessor, SmartLifecycle {
 
 	private final ManagementContextFactory managementContextFactory;
 
@@ -64,6 +64,8 @@ class ChildManagementContextInitializer
 
 	private final ApplicationContextInitializer<ConfigurableApplicationContext> applicationContextInitializer;
 
+	private volatile ConfigurableApplicationContext managementContext;
+
 	ChildManagementContextInitializer(ManagementContextFactory managementContextFactory,
 			ApplicationContext parentContext) {
 		this(managementContextFactory, parentContext, null);
@@ -79,12 +81,33 @@ class ChildManagementContextInitializer
 	}
 
 	@Override
-	public void onApplicationEvent(WebServerInitializedEvent event) {
-		if (event.getApplicationContext().equals(this.parentContext)) {
+	public void start() {
+		if (this.managementContext == null) {
 			ConfigurableApplicationContext managementContext = createManagementContext();
 			registerBeans(managementContext);
 			managementContext.refresh();
+			this.managementContext = managementContext;
 		}
+		else {
+			this.managementContext.start();
+		}
+	}
+
+	@Override
+	public void stop() {
+		if (this.managementContext != null) {
+			this.managementContext.stop();
+		}
+	}
+
+	@Override
+	public boolean isRunning() {
+		return this.managementContext != null && this.managementContext.isRunning();
+	}
+
+	@Override
+	public int getPhase() {
+		return WebServerGracefulShutdownLifecycle.SMART_LIFECYCLE_PHASE + 512;
 	}
 
 	@Override
diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/web/server/ManagementContextAutoConfigurationTests.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/web/server/ManagementContextAutoConfigurationTests.java
index 1d4e7c7319..52fca8b17a 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/web/server/ManagementContextAutoConfigurationTests.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/web/server/ManagementContextAutoConfigurationTests.java
@@ -55,6 +55,21 @@ class ManagementContextAutoConfigurationTests {
 			.run((context) -> assertThat(output).satisfies(numberOfOccurrences("Tomcat started on port", 2)));
 	}
 
+	@Test
+	void childManagementContextShouldRestartWhenParentIsStoppedThenStarted(CapturedOutput output) {
+		WebApplicationContextRunner contextRunner = new WebApplicationContextRunner(
+				AnnotationConfigServletWebServerApplicationContext::new)
+			.withConfiguration(AutoConfigurations.of(ManagementContextAutoConfiguration.class,
+					ServletWebServerFactoryAutoConfiguration.class, ServletManagementContextAutoConfiguration.class,
+					WebEndpointAutoConfiguration.class, EndpointAutoConfiguration.class));
+		contextRunner.withPropertyValues("server.port=0", "management.server.port=0").run((context) -> {
+			assertThat(output).satisfies(numberOfOccurrences("Tomcat started on port", 2));
+			context.getSourceApplicationContext().stop();
+			context.getSourceApplicationContext().start();
+			assertThat(output).satisfies(numberOfOccurrences("Tomcat started on port", 4));
+		});
+	}
+
 	@Test
 	void givenSamePortManagementServerWhenManagementServerAddressIsConfiguredThenContextRefreshFails() {
 		WebApplicationContextRunner contextRunner = new WebApplicationContextRunner(