Permissions Bug in OLS

I have a very strange problem with OLS. Everytime my wordpress site needs updates it says Files could not be installed due to likely permission errors.

Nothing fixes the problem unless I go ssh in and do the following command
sudo chown -R nobody:nogroup /usr/local/lsws/Example/html/wordpress

The thing is… when I stat the wordpress directory it already belongs to nobody:nogroup with the correct permission level.

The Vhost running on OLS is also Nobody