Proxy awareness with pip

I have tried to set up a python development environment at my work place to create some basic applications. I can’t seem to get pip to work, for example I type in pip install numpy and get the following error message:

How to use pip on windows behind an authenticating proxy

My computer is running windows behind a proxy on a windows server (using active directory), and I can’t figure out how to get through it with pip (in python3). I have tried using --proxy, but it still just timeouts. I have also tried setting a long timeout (60s), but that made no difference. My proxy settings are correct, and I compared them with those that I’m using successfully in TortoiseHG to make sure.

Tunnel traffic through another machine over ssh

I want to be able to route a portion of my traffic through another machine over SSH. For example, is it possible to browse the web through the ssh tunnel and also browse the web through your LAN connection without much effort? (i.e. I want a seamless transition from using tunnel to using LAN)

Automatically reconnect to ssh after suspend

I’m using ssh as a SOCKS5 proxy, connecting to my personal server. When my system is suspended or I lose internet connection, the ssh will eventually time out, forcing me to manually reconnect. How can I configure my system to automatically reconnect as soon as an internet connection is established?