diff --git a/x-pack/plugins/reporting/server/deprecations/reporting_role.ts b/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
index a9ea10a6c2949..31633760aeb84 100644
--- a/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
+++ b/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
@@ -211,7 +211,7 @@ async function getRoleMappingsDeprecations(
   const roleMappingsWithReportingRole: string[] = Object.entries(roleMappings).reduce(
     (roleSet, current) => {
       const [roleName, role] = current;
-      const foundMapping = role.roles.find((roll) => deprecatedRoles.includes(roll));
+      const foundMapping = role.roles?.find((roll) => deprecatedRoles.includes(roll));
       if (foundMapping) {
         roleSet.push(`${roleName}[${foundMapping}]`);
       }
diff --git a/x-pack/plugins/security/server/deprecations/kibana_user_role.ts b/x-pack/plugins/security/server/deprecations/kibana_user_role.ts
index f6c3cc4113ed7..f5ce027b8b2dc 100644
--- a/x-pack/plugins/security/server/deprecations/kibana_user_role.ts
+++ b/x-pack/plugins/security/server/deprecations/kibana_user_role.ts
@@ -156,7 +156,7 @@ async function getRoleMappingsDeprecations(
   }
 
   const roleMappingsWithKibanaUserRole = Object.entries(roleMappings)
-    .filter(([, roleMapping]) => roleMapping.roles.includes(KIBANA_USER_ROLE_NAME))
+    .filter(([, roleMapping]) => roleMapping.roles?.includes(KIBANA_USER_ROLE_NAME))
     .map(([mappingName]) => mappingName);
   if (roleMappingsWithKibanaUserRole.length === 0) {
     return [];
diff --git a/x-pack/plugins/security/server/routes/deprecations/kibana_user_role.ts b/x-pack/plugins/security/server/routes/deprecations/kibana_user_role.ts
index 036d1f141f997..2df81edf2d75b 100644
--- a/x-pack/plugins/security/server/routes/deprecations/kibana_user_role.ts
+++ b/x-pack/plugins/security/server/routes/deprecations/kibana_user_role.ts
@@ -100,7 +100,7 @@ export function defineKibanaUserRoleDeprecationRoutes({ router, logger }: RouteD
       }
 
       const roleMappingsWithKibanaUserRole = Object.entries(roleMappings).filter(([, mapping]) =>
-        mapping.roles.includes(KIBANA_USER_ROLE_NAME)
+        mapping.roles?.includes(KIBANA_USER_ROLE_NAME)
       );
 
       if (roleMappingsWithKibanaUserRole.length === 0) {