Using Windows Subsystem for Linux (WSL) can be a great tool for dev's, op's, and admin's alike. The downside often these roles are after larger organization that gave Firewalls and tight proxy security.
I found myself in this exact situation. The corp. proxy uses a *.pac file script. Nothing in the Debian world does. Ugg. Here is how I got Debian apt to work behind a proxy.
Original Solution Source from the Linux Questions Forums.
wget http://some.domain.tld/some-proxy.pac
...or you can probably just open it with a browser.
Look for the proxy address that is used if all other options fail. Typically towards the bottom / in a function call of its own.
function FindProxyForURL(url, host) { return "PROXY proxy.foo.com:8080; DIRECT"; }
Take note of the URL:PORT address.
Finally, put this in your /etc/apt/apt.conf file:
Acquire::http::Proxy "http://proxy.foo.com:8080";
Log out and back in. At this point apt-get update -y and related apt commands should work as expected.
good