Wordpress behind a proxy - communication errors

So, I am an internal webmaster/web designer/developer for a government agency’s website and here is the scenario:

I’m not getting much help form internal IT because they don’t know Apache and PHP…

I asked that the server be switched to IS and that Microsoft Web Platform Installer be installed, so that they could be more familiar with the server set up and be able to assist but I’m currently waiting for a ‘bureacratic formality’ that has to precede the installation of Windows 2012 server, instead of Windows 2008 that is currently there. I’m hoping that Windows 2012 would better facilitate the MS Web Platform Installer installation.

So the problem is this, because I quite suspect that the ‘bureacratic formality’ will take forever, so in the meantime, I’m trying to enable two-way communication to the server by opening a way through the proxy.

I’m trying to add this via wp-config.php

define(‘WP_PROXY_HOST’, ‘’);
define(‘WP_PROXY_PORT’, ‘80’);
define(‘WP_PROXY_USER’, ‘’);
define(‘WP_PROXY_PASS’, ‘’);
define (‘WP_USEPROXY’, true);

One of the IT guys told me to try the Proxies:

(I asked why 3 and he said that the server tries each one until it gets through…)

…but it’s not seeming to work because trying to install a plugin, I’m getting errors (- see image attached below). I can tell that there are communication errors on the server, because other plugins such as Wordfence cannot communicate with their servers…

I"m trying to figure out what I may be doing wrong because I really think that editing WordPress to get through the proxy could work…

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