diff --git a/engine/e2e-test/main.py b/engine/e2e-test/main.py
index d59466d29..9ef27c8dc 100644
--- a/engine/e2e-test/main.py
+++ b/engine/e2e-test/main.py
@@ -4,6 +4,8 @@
 from test_cli_engine_install import TestCliEngineInstall
 from test_cli_engine_list import TestCliEngineList
 from test_cli_engine_uninstall import TestCliEngineUninstall
+from test_cli_server_start import TestCliServerStart
+from test_create_log_folder import TestCreateLogFolder
 
 if __name__ == "__main__":
     pytest.main([__file__, "-v"])
diff --git a/engine/e2e-test/test_cli_server_start.py b/engine/e2e-test/test_cli_server_start.py
new file mode 100644
index 000000000..abe236cd0
--- /dev/null
+++ b/engine/e2e-test/test_cli_server_start.py
@@ -0,0 +1,24 @@
+import platform
+import os
+import pytest, requests
+from test_runner import run
+from test_runner import start_server, stop_server
+
+
+class TestCliServerStart:
+
+    @pytest.fixture(autouse=True)
+    def setup_and_teardown(self):
+        # Setup
+        success = start_server()
+        if not success:
+            raise Exception("Failed to start server")
+
+        yield
+
+        # Teardown
+        stop_server()
+
+    def test_server_start_cli_run_successfully(self):
+        response = requests.get("http://localhost:3928/healthz")
+        assert response.status_code == 200
diff --git a/engine/e2e-test/test_create_log_folder.py b/engine/e2e-test/test_create_log_folder.py
new file mode 100644
index 000000000..3d0236cd7
--- /dev/null
+++ b/engine/e2e-test/test_create_log_folder.py
@@ -0,0 +1,27 @@
+import platform
+import os
+from pathlib import Path
+import pytest, requests, shutil
+from test_runner import run
+from test_runner import start_server, stop_server
+
+
+class TestCreateLogFolder:
+    @pytest.fixture(autouse=True)
+    def setup_and_teardown(self):
+        # Setup
+        root = Path.home()
+        if os.path.exists(root / "cortexcpp" / "logs"):
+            shutil.rmtree(root / "cortexcpp" / "logs")
+        success = start_server()
+        if not success:
+            raise Exception("Failed to start server")
+
+        yield
+
+        # Teardown
+        stop_server()
+
+    def test_create_log_folder_run_successfully(self):
+        root = Path.home()
+        assert os.path.exists(root / "cortexcpp" / "logs")
diff --git a/engine/main.cc b/engine/main.cc
index 949f9e0d2..38dd3791b 100644
--- a/engine/main.cc
+++ b/engine/main.cc
@@ -31,8 +31,8 @@ void RunServer() {
            << " Port: " << config.apiServerPort << "\n";
 
   // Create logs/ folder and setup log to file
-  std::filesystem::create_directory(config.logFolderPath + "/" +
-                                    cortex_utils::logs_folder);
+  std::filesystem::create_directories(std::filesystem::path(config.logFolderPath) /
+                                    std::filesystem::path(cortex_utils::logs_folder));
   trantor::FileLogger asyncFileLogger;
   asyncFileLogger.setFileName(config.logFolderPath + "/" +
                               cortex_utils::logs_base_name);
@@ -160,6 +160,8 @@ int main(int argc, char* argv[]) {
       return 0;
     } else {
       auto config = file_manager_utils::GetCortexConfig();
+      std::filesystem::create_directories(std::filesystem::path(config.logFolderPath) /
+                                    std::filesystem::path(cortex_utils::logs_folder));
       trantor::FileLogger asyncFileLogger;
       asyncFileLogger.setFileName(config.logFolderPath + "/" +
                                   cortex_utils::logs_cli_base_name);