diff --git a/test/paths.sort.spec.ts b/test/paths.sort.spec.ts
new file mode 100644
index 00000000..6d2fc4fa
--- /dev/null
+++ b/test/paths.sort.spec.ts
@@ -0,0 +1,44 @@
+import {
+  sortRoutes,
+} from '../src/framework/openapi.spec.loader';
+import { expect } from 'chai';
+
+describe('url sorter', () => {
+  it('should sort dynamic leafs after static leafs', async () => {
+    const urls = asRouteMetadatas(['/my/:id', '/my/path']);
+    const expected = ['/my/path', '/my/:id'];
+
+    urls.sort(sortRoutes);
+
+    expect(urls[0].expressRoute).to.equal(expected[0]);
+    expect(urls[1].expressRoute).to.equal(expected[1]);
+  });
+
+  it('should sort dynamic inner paths after static inner paths', async () => {
+    const urls = asRouteMetadatas([
+      '/my/:id/test',
+      '/my/path/test',
+      '/a/:b/c/:d',
+      '/a/:b/c/d',
+    ]);
+    const expected = [
+      '/a/:b/c/d',
+      '/a/:b/c/:d',
+      '/my/path/test',
+      '/my/:id/test',
+    ];
+
+    urls.sort(sortRoutes);
+
+    expect(urls[0].expressRoute).to.equal(expected[0]);
+    expect(urls[1].expressRoute).to.equal(expected[1]);
+    expect(urls[2].expressRoute).to.equal(expected[2]);
+    expect(urls[3].expressRoute).to.equal(expected[3]);
+  });
+});
+
+function asRouteMetadatas(urls: string[]) {
+  return urls.map(u => ({
+    expressRoute: u,
+  }));
+}