tumic
10
The webshield was ON too, when you executed the lsof command the last time, this is visible from the output. But the problem can not be caused by exhausting the file descriptors as I suggested from the system log you pasted, if lsof was executed at the moment when the webshield does not work.
The problem must be somewhere else. Do you have some kind of firewall set up? What does the command
sudo ipfw list
(ipfw list executed as root)
show? And can you post here the whole output of
grep proxy /var/log/system.log