diff --git a/netboxlabs/diode/sdk/client.py b/netboxlabs/diode/sdk/client.py
index 429cab5..f9f94b1 100644
--- a/netboxlabs/diode/sdk/client.py
+++ b/netboxlabs/diode/sdk/client.py
@@ -237,7 +237,7 @@ def ingest(
                         self._authenticate()
                         continue
                 raise DiodeClientError(err) from err
-        return RuntimeError("Max retries exceeded")
+        raise RuntimeError("Max retries exceeded")
 
     def _setup_sentry(self, dsn: str, traces_sample_rate: float, profiles_sample_rate: float):
         sentry_sdk.init(
@@ -289,8 +289,11 @@ def authenticate(self) -> str:
             }
         )
         url = self._get_auth_url()
-        conn.request("POST", url, data, headers)
-        response = conn.getresponse()
+        try:
+            conn.request("POST", url, data, headers)
+            response = conn.getresponse()
+        except Exception as e:
+            raise DiodeConfigError(f"Failed to obtain access token: {e}")
         if response.status != 200:
             raise DiodeConfigError(f"Failed to obtain access token: {response.reason}")
         token_info = json.loads(response.read().decode())
diff --git a/tests/test_client.py b/tests/test_client.py
index 4cc510e..e8383eb 100644
--- a/tests/test_client.py
+++ b/tests/test_client.py
@@ -588,6 +588,7 @@ def test_diode_authentication_failure(mock_diode_authentication):
             auth.authenticate()
         assert "Failed to obtain access token" in str(excinfo.value)
 
+
 @pytest.mark.parametrize("path", [
     "/diode",
     "",
@@ -612,3 +613,21 @@ def test_diode_authentication_url_with_path(mock_diode_authentication, path):
         auth.authenticate()
         mock_conn_instance.request.assert_called_once_with("POST", f"{(path or '').rstrip('/')}/auth/token", mock.ANY, mock.ANY)
 
+
+def test_diode_authentication_request_exception(mock_diode_authentication):
+    """Test that an exception during the request raises a DiodeConfigError."""
+    auth = _DiodeAuthentication(
+        target="localhost:8081",
+        path="/diode",
+        tls_verify=False,
+        client_id="test_client_id",
+        client_secret="test_client_secret",
+    )
+    with mock.patch("http.client.HTTPConnection") as mock_http_conn:
+        mock_conn_instance = mock_http_conn.return_value
+        mock_conn_instance.request.side_effect = Exception("Connection error")
+
+        with pytest.raises(DiodeConfigError) as excinfo:
+            auth.authenticate()
+        assert "Failed to obtain access token: Connection error" in str(excinfo.value)
+