diff --git a/packages/kbn-router-to-openapispec/src/util.test.ts b/packages/kbn-router-to-openapispec/src/util.test.ts
index e3011aa1a5a73..ee34976e47152 100644
--- a/packages/kbn-router-to-openapispec/src/util.test.ts
+++ b/packages/kbn-router-to-openapispec/src/util.test.ts
@@ -117,10 +117,12 @@ describe('assignToPaths', () => {
     assignToPaths(paths, '/foo', {});
     assignToPaths(paths, '/bar/{id?}', {});
     assignToPaths(paths, '/bar/file/{path*}', {});
+    assignToPaths(paths, '/bar/file/{path*}/{id?}', {});
     expect(paths).toEqual({
       '/foo': {},
       '/bar/{id}': {},
       '/bar/file/{path}': {},
+      '/bar/file/{path}/{id}': {},
     });
   });
 });
diff --git a/packages/kbn-router-to-openapispec/src/util.ts b/packages/kbn-router-to-openapispec/src/util.ts
index 1088259e73d05..61c69caf538f9 100644
--- a/packages/kbn-router-to-openapispec/src/util.ts
+++ b/packages/kbn-router-to-openapispec/src/util.ts
@@ -132,7 +132,7 @@ export const assignToPaths = (
   path: string,
   pathObject: OpenAPIV3.PathItemObject
 ): void => {
-  const pathName = path.replace(/[\?\*]/, '');
+  const pathName = path.replace(/[\?\*]/g, '');
   paths[pathName] = { ...paths[pathName], ...pathObject };
 };