diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/servlet/ServletManagementChildContextConfiguration.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/servlet/ServletManagementChildContextConfiguration.java
index f5e8a31009..159bcf49a9 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/servlet/ServletManagementChildContextConfiguration.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/web/servlet/ServletManagementChildContextConfiguration.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.
@@ -50,6 +50,7 @@ import org.springframework.boot.web.embedded.jetty.JettyServletWebServerFactory;
 import org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory;
 import org.springframework.boot.web.embedded.undertow.UndertowServletWebServerFactory;
 import org.springframework.boot.web.server.WebServerFactoryCustomizer;
+import org.springframework.boot.web.servlet.DelegatingFilterProxyRegistrationBean;
 import org.springframework.boot.web.servlet.server.ConfigurableServletWebServerFactory;
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
@@ -108,6 +109,13 @@ class ServletManagementChildContextConfiguration {
 			return parent.getBean(BeanIds.SPRING_SECURITY_FILTER_CHAIN, Filter.class);
 		}
 
+		@Bean
+		@ConditionalOnBean(name = "securityFilterChainRegistration", search = SearchStrategy.ANCESTORS)
+		DelegatingFilterProxyRegistrationBean securityFilterChainRegistration(HierarchicalBeanFactory beanFactory) {
+			return beanFactory.getParentBeanFactory().getBean("securityFilterChainRegistration",
+					DelegatingFilterProxyRegistrationBean.class);
+		}
+
 	}
 
 	static class ServletManagementWebServerFactoryCustomizer
diff --git a/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-actuator/src/test/java/smoketest/actuator/ManagementPortSampleActuatorApplicationTests.java b/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-actuator/src/test/java/smoketest/actuator/ManagementPortSampleActuatorApplicationTests.java
index eddf529511..f69f1001c9 100644
--- a/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-actuator/src/test/java/smoketest/actuator/ManagementPortSampleActuatorApplicationTests.java
+++ b/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-actuator/src/test/java/smoketest/actuator/ManagementPortSampleActuatorApplicationTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2019 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.
@@ -19,14 +19,22 @@ package smoketest.actuator;
 import java.util.Map;
 
 import org.junit.jupiter.api.Test;
+import smoketest.actuator.ManagementPortSampleActuatorApplicationTests.CustomErrorAttributes;
 
+import org.springframework.beans.factory.annotation.Autowired;
 import org.springframework.boot.actuate.autoconfigure.web.server.LocalManagementPort;
 import org.springframework.boot.test.context.SpringBootTest;
 import org.springframework.boot.test.context.SpringBootTest.WebEnvironment;
 import org.springframework.boot.test.web.client.TestRestTemplate;
+import org.springframework.boot.web.error.ErrorAttributeOptions;
 import org.springframework.boot.web.server.LocalServerPort;
+import org.springframework.boot.web.servlet.error.DefaultErrorAttributes;
+import org.springframework.context.annotation.Import;
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
+import org.springframework.security.core.context.SecurityContext;
+import org.springframework.security.core.context.SecurityContextHolder;
+import org.springframework.web.context.request.WebRequest;
 
 import static org.assertj.core.api.Assertions.assertThat;
 
@@ -37,6 +45,7 @@ import static org.assertj.core.api.Assertions.assertThat;
  */
 @SpringBootTest(webEnvironment = WebEnvironment.RANDOM_PORT,
 		properties = { "management.server.port=0", "management.endpoint.health.show-details=always" })
+@Import(CustomErrorAttributes.class)
 class ManagementPortSampleActuatorApplicationTests {
 
 	@LocalServerPort
@@ -45,6 +54,9 @@ class ManagementPortSampleActuatorApplicationTests {
 	@LocalManagementPort
 	private int managementPort;
 
+	@Autowired
+	private CustomErrorAttributes errorAttributes;
+
 	@Test
 	void testHome() {
 		ResponseEntity<Map<String, Object>> entity = asMapEntity(
@@ -79,9 +91,31 @@ class ManagementPortSampleActuatorApplicationTests {
 		assertThat(entity.getBody().get("status")).isEqualTo(999);
 	}
 
+	@Test
+	void securityContextIsAvailableToErrorHandling() {
+		this.errorAttributes.securityContext = null;
+		ResponseEntity<Map<String, Object>> entity = asMapEntity(new TestRestTemplate("user", "password")
+				.getForEntity("http://localhost:" + this.managementPort + "/404", Map.class));
+		assertThat(this.errorAttributes.securityContext.getAuthentication()).isNotNull();
+		assertThat(entity.getStatusCode()).isEqualTo(HttpStatus.NOT_FOUND);
+		assertThat(entity.getBody().get("status")).isEqualTo(404);
+	}
+
 	@SuppressWarnings({ "unchecked", "rawtypes" })
 	static <K, V> ResponseEntity<Map<K, V>> asMapEntity(ResponseEntity<Map> entity) {
 		return (ResponseEntity) entity;
 	}
 
+	static class CustomErrorAttributes extends DefaultErrorAttributes {
+
+		private volatile SecurityContext securityContext;
+
+		@Override
+		public Map<String, Object> getErrorAttributes(WebRequest webRequest, ErrorAttributeOptions options) {
+			this.securityContext = SecurityContextHolder.getContext();
+			return super.getErrorAttributes(webRequest, options);
+		}
+
+	}
+
 }