iOS's Safari and iPFire Proxy

Aside from your suggestion regarding OVPN I played around with iOS a bit and I wonder why when setting up eg. 192.168.1.1:800 for the green proxy on my iOS’s wirelesss network (on BLUE) everything works in contrast to using 192.168.2.1:800 for the blue proxy.

I’d really like to know what I need to configure to get the proxy working fine on BLUE. It seems to me it doesn’t have to do with wpad settings anyway.

A good hint would greatly be appreciated.