diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/EnterpriseEndpointFilter.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/EnterpriseEndpointFilter.java
index 22c56aecd..a0165a28c 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/EnterpriseEndpointFilter.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/EnterpriseEndpointFilter.java
@@ -28,11 +28,19 @@ public class EnterpriseEndpointFilter extends OncePerRequestFilter {
         if (!runningProOrHigher && isPrometheusEndpointRequest(request)) {
             // Allow only health checks to pass through for non-pro users
             String uri = request.getRequestURI();
+
+            // Strip the context path
+            String contextPath = request.getContextPath();
+            String trimmedUri =
+                    (contextPath != null && uri.startsWith(contextPath))
+                            ? uri.substring(contextPath.length())
+                            : uri;
+
             boolean isHealthCheck =
-                    uri.contains("/actuator/health")
-                            || uri.contains("/healthz")
-                            || uri.contains("/liveness")
-                            || uri.contains("/readiness");
+                    trimmedUri.startsWith("/actuator/health")
+                            || "/healthz".equals(trimmedUri)
+                            || "/liveness".equals(trimmedUri)
+                            || "/readiness".equals(trimmedUri);
 
             if (!isHealthCheck) {
                 response.setStatus(HttpStatus.NOT_FOUND.value());