diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/reactive/EndpointRequest.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/reactive/EndpointRequest.java
index 2801342b2d..7d98fdeb2f 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/reactive/EndpointRequest.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/reactive/EndpointRequest.java
@@ -130,6 +130,8 @@ public final class EndpointRequest {
 
 		private volatile ServerWebExchangeMatcher delegate;
 
+		private static ManagementPortType managementPortType;
+
 		private EndpointServerWebExchangeMatcher(boolean includeLinks) {
 			this(Collections.emptyList(), Collections.emptyList(), includeLinks);
 		}
@@ -231,7 +233,10 @@ public final class EndpointRequest {
 
 		static boolean isManagementContext(ServerWebExchange exchange) {
 			ApplicationContext applicationContext = exchange.getApplicationContext();
-			if (ManagementPortType.get(applicationContext.getEnvironment()) == ManagementPortType.DIFFERENT) {
+			if (managementPortType == null) {
+				managementPortType = ManagementPortType.get(applicationContext.getEnvironment());
+			}
+			if (managementPortType == ManagementPortType.DIFFERENT) {
 				if (applicationContext.getParent() == null) {
 					return false;
 				}
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 eef4c055ce..fc88ba4b32 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
@@ -124,14 +124,18 @@ public final class EndpointRequest {
 
 		private volatile RequestMatcher delegate;
 
+		private static ManagementPortType managementPortType;
+
 		AbstractRequestMatcher() {
 			super(WebApplicationContext.class);
 		}
 
 		@Override
 		protected boolean ignoreApplicationContext(WebApplicationContext applicationContext) {
-			ManagementPortType type = ManagementPortType.get(applicationContext.getEnvironment());
-			return type == ManagementPortType.DIFFERENT
+			if (managementPortType == null) {
+				managementPortType = ManagementPortType.get(applicationContext.getEnvironment());
+			}
+			return managementPortType == ManagementPortType.DIFFERENT
 					&& !WebServerApplicationContext.hasServerNamespace(applicationContext, "management");
 		}