diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequest.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequest.java
index 1ab763653f3..295f3d76f51 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequest.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequest.java
@@ -185,8 +185,14 @@ public final class EndpointRequest {
 		protected final boolean hasWebServerNamespace(ApplicationContext applicationContext,
 				WebServerNamespace webServerNamespace) {
 			return WebServerApplicationContext.hasServerNamespace(applicationContext, webServerNamespace.getValue())
-					|| (webServerNamespace.equals(WebServerNamespace.SERVER)
-							&& !(applicationContext instanceof WebServerApplicationContext));
+					|| hasImplicitServerNamespace(applicationContext, webServerNamespace);
+		}
+
+		private boolean hasImplicitServerNamespace(ApplicationContext applicationContext,
+				WebServerNamespace webServerNamespace) {
+			return WebServerNamespace.SERVER.equals(webServerNamespace)
+					&& WebServerApplicationContext.getServerNamespace(applicationContext) == null
+					&& applicationContext.getParent() == null;
 		}
 
 		@Override
diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequestTests.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequestTests.java
index ebb958bf385..3c112666eff 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequestTests.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/EndpointRequestTests.java
@@ -349,9 +349,12 @@ class EndpointRequestTests {
 	}
 
 	private RequestMatcherAssert assertMatcher(RequestMatcher matcher, PathMappedEndpoints pathMappedEndpoints,
-			RequestMatcherProvider matcherProvider, WebServerNamespace webServerNamespace) {
-		StaticWebApplicationContext context = (webServerNamespace != null)
-				? new NamedStaticWebApplicationContext(webServerNamespace) : new StaticWebApplicationContext();
+			RequestMatcherProvider matcherProvider, WebServerNamespace namespace) {
+		StaticWebApplicationContext context = new StaticWebApplicationContext();
+		if (namespace != null && !WebServerNamespace.SERVER.equals(namespace)) {
+			NamedStaticWebApplicationContext parentContext = new NamedStaticWebApplicationContext(namespace);
+			context.setParent(parentContext);
+		}
 		context.registerBean(WebEndpointProperties.class);
 		if (pathMappedEndpoints != null) {
 			context.registerBean(PathMappedEndpoints.class, () -> pathMappedEndpoints);
@@ -382,7 +385,7 @@ class EndpointRequestTests {
 
 		@Override
 		public String getServerNamespace() {
-			return this.webServerNamespace.getValue();
+			return (this.webServerNamespace != null) ? this.webServerNamespace.getValue() : null;
 		}
 
 	}