diff --git a/core/server/services/auth/authorize.js b/core/server/services/auth/authorize.js
index 05cefaca0c..ef8189a142 100644
--- a/core/server/services/auth/authorize.js
+++ b/core/server/services/auth/authorize.js
@@ -52,7 +52,8 @@ const authorize = {
             return next();
         }
         return next(new common.errors.NoPermissionError({
-            message: common.i18n.t('errors.middleware.auth.pleaseSignInOrAuthenticate')
+            message: common.i18n.t('errors.middleware.auth.authorizationFailed'),
+            context: common.i18n.t('errors.middleware.auth.missingContentMemberOrIntegration')
         }));
     },
 
@@ -70,7 +71,8 @@ const authorize = {
             return next();
         } else {
             return next(new common.errors.NoPermissionError({
-                message: common.i18n.t('errors.middleware.auth.pleaseSignInOrAuthenticate')
+                message: common.i18n.t('errors.middleware.auth.authorizationFailed'),
+                context: common.i18n.t('errors.middleware.auth.missingAdminUserOrIntegration')
             }));
         }
     }
diff --git a/core/server/translations/en.json b/core/server/translations/en.json
index 350d6a014d..cea78c9d18 100644
--- a/core/server/translations/en.json
+++ b/core/server/translations/en.json
@@ -78,7 +78,9 @@
                 "missingUserIDForSession": "Cannot create session without user id.",
                 "accessDenied": "Access denied.",
                 "pleaseSignIn": "Please Sign In",
-                "pleaseSignInOrAuthenticate": "Please sign in or authenticate with an API Key",
+                "authorizationFailed": "Authorization failed",
+                "missingContentMemberOrIntegration": "Unable to determine the authenticated member or integration. Check the supplied Content API Key and ensure cookies are being passed through if member auth is failing.",
+                "missingAdminUserOrIntegration": "Unable to determine the authenticated user or integration. Check that cookies are being passed through if using session authentication.",
                 "adminApiKeyMissing": "Admin API Key missing.",
                 "unknownAdminApiKey": "Unknown Admin API Key",
                 "unknownContentApiKey": "Unknown Content API Key",