diff --git a/guardrails/cli/configure.py b/guardrails/cli/configure.py
index a8739227a..11ffdaad7 100644
--- a/guardrails/cli/configure.py
+++ b/guardrails/cli/configure.py
@@ -43,6 +43,8 @@ def save_configuration_file(
         rc_file.writelines(lines)
         rc_file.close()
 
+    settings._initialize()
+
 
 def _get_default_token() -> str:
     """Get the default token from the configuration file."""
@@ -106,6 +108,7 @@ def configure(
 
     try:
         save_configuration_file(token, enable_metrics, remote_inferencing)
+        # update setting singleton
         logger.info("Configuration saved.")
     except Exception as e:
         logger.error("An unexpected error occured saving configuration!")
diff --git a/tests/unit_tests/cli/test_configure.py b/tests/unit_tests/cli/test_configure.py
index fc043462f..e241fa0f7 100644
--- a/tests/unit_tests/cli/test_configure.py
+++ b/tests/unit_tests/cli/test_configure.py
@@ -69,6 +69,9 @@ def test_save_configuration_file(mocker):
     expanduser_mock = mocker.patch("guardrails.cli.configure.expanduser")
     expanduser_mock.return_value = "/Home"
 
+    rcexpanduser_mock = mocker.patch("guardrails.classes.rc.expanduser")
+    rcexpanduser_mock.return_value = "/Home"
+
     import os
 
     join_spy = mocker.spy(os.path, "join")
@@ -88,7 +91,9 @@ def test_save_configuration_file(mocker):
     save_configuration_file("token", True)
 
     assert expanduser_mock.called is True
-    join_spy.assert_called_once_with("/Home", ".guardrailsrc")
+    assert rcexpanduser_mock.called is True
+    join_spy.assert_called_with("/Home", ".guardrailsrc")
+    assert join_spy.call_count == 2
 
     assert mock_open.call_count == 1
     writelines_spy.assert_called_once_with(