It might help if you could characterize what "isn't 100% reliable" means in your situation.

Usually the proxy software (squid) dies and refuses connections. Occasionally the machine itself locks up, but I'm primarily worried about squid dying.

Read the code.

I thought that's what documentation is for? :)

What I'm most confused about is what 'timeout' means when using a proxy. How can I set the timeout such that if the proxy connects to a slow site, I don't time out. But if the proxy doesn't respond, I do time out? Or are these issues not visible to the agent?

-- Dave