diff --git a/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/ActuatorSecurityConfig.java b/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/ActuatorSecurityConfig.java
index 727d819..8aed60a 100644
--- a/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/ActuatorSecurityConfig.java
+++ b/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/ActuatorSecurityConfig.java
@@ -2,9 +2,11 @@ package com.hithomelabs.cftunnels.Config.Security;
 
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
+import org.springframework.core.Ordered;
 import org.springframework.core.annotation.Order;
 import org.springframework.security.config.annotation.web.builders.HttpSecurity;
 import org.springframework.security.web.SecurityFilterChain;
+import org.springframework.boot.actuate.autoconfigure.security.servlet.EndpointRequest;
 
 /**
  * Security configuration for Spring Boot Actuator endpoints.
@@ -12,15 +14,20 @@ import org.springframework.security.web.SecurityFilterChain;
  * This configuration permits unauthenticated access to /actuator/health and /actuator/info
  * endpoints, enabling health monitoring by Uptime Kuma without requiring OIDC authentication.
  * All other actuator endpoints remain protected and require authentication.
+ *
+ * Uses @Order(Ordered.HIGHEST_PRECEDENCE) to ensure this filter chain is evaluated BEFORE
+ * any auto-configured management security filter chains (e.g., ManagementWebSecurityAutoConfiguration).
+ * Without this, the catch-all SecurityFilterChain in SecuirtyConfig can intercept actuator
+ * requests on the separate management port (management.server.port=8081) and redirect to OIDC login.
  */
 @Configuration
+@Order(Ordered.HIGHEST_PRECEDENCE)
 public class ActuatorSecurityConfig {
 
     @Bean
-    @Order(1)
     public SecurityFilterChain actuatorSecurityChain(HttpSecurity http) throws Exception {
         http
-                .securityMatcher("/actuator/**")
+                .securityMatcher(EndpointRequest.toAnyEndpoint())
                 .authorizeHttpRequests(auth -> auth
                         .requestMatchers("/actuator/health", "/actuator/info").permitAll()
                         .anyRequest().authenticated()
diff --git a/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/SecuirtyConfig.java b/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/SecuirtyConfig.java
index 6dd3073..2f004e7 100644
--- a/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/SecuirtyConfig.java
+++ b/cftunnels-service/src/main/java/com/hithomelabs/cftunnels/Config/Security/SecuirtyConfig.java
@@ -29,6 +29,7 @@ public class SecuirtyConfig {
         http
                 .authorizeHttpRequests(auth -> auth
                         //.requestMatchers( "/v3/api-docs/**", "/swagger-ui/**", "/swagger-ui.html" ).permitAll()
+                        .requestMatchers("/actuator/health", "/actuator/info").permitAll()
                         .anyRequest().authenticated()
                 ).csrf(csrf -> csrf.disable())
                 .with(new OAuth2LoginConfigurer<>(),