In short, if Box Drive sees a proxy and attempts to connect via the proxy but that fails, it should fall back and attempt a direct connection before failing completely.

I experienced this on Windows. Not sure if it would apply to other OSes or not.

The specific details...

I'm in a Corporate environment with a laptop. When our laptops are on the corporate network, we do go through a proxy. But when off of the corporate network, like working at home, it doesn't use the proxy. We use an auto-config proxy .pac file to control the proxy on and off the network. This works for most things.

HOWEVER, I also have some system environment variables defined on my computer, HTTPPROXY and HTTPSPROXY, that are required to make some of our cloud development tools work, like for AWS, on our corporate network.

Box Drive apparently also sees these environment variables and attempts to use the proxy even when I'm outside our Corporate network. The environment variables appear to override the auto-config proxy .pac config. Since the corporate proxy is not accessible outside the corporate network, the Box Drive client fails to connect outside the corporate network.

If I delete the HTTPPROXY and HTTPSPROXY environment variables, then Box Drive connects correctly outside of the corporate network.

There may be other solutions too, but the first thing I thought of was that if a proxy connection fails, fall back to attempt a direct connection.