Update again, for those following along or who encounter this in the future
ERROR: No response received from remote node after 2.37 minutes, giving up.
Access Denied
ERROR: Exception: Unable to parse authorization header. Headers: {"Proxy-Authenticate"=>"NTLM", "Cache-Control"=>"no-cache", "Pragma"=>"no-cache", "Content-Type"=>"text/html; charset=utf-8", "Proxy-Connection"=>"close", "Set-Cookie"=>"BCSI-CS-477914e091836061=2; Path=/", "Connection"=>"close", "Content-Length"=>"1106"}
Body:
Your credentials could not be authenticated: "General authentication failure due to bad user ID or authentication token." You will not be permitted access until your credentials can be verified.
This is typically caused by an incorrect username and/or password, but could also be caused by network problems.
If you have any questions please contact desktopsupport@blah.com
That looks like I'm reaching the proxy but the authentication is just failing so I think I'm close. I found this page - Working with Proxies - which makes reference to updating your knife.rb to include these entries
http_proxy myproxyip:proxyport
http_proxy_pass mywindowscredsforproxy
http_proxy_user mywindowspass
Our proxy uses NTLM I think so its just a matter of formatting at this point. I'm working with our networking team that manages the proxy but I think once I get it added to knife.rb correctly, we should be in business. Once I get it working I plan on recapping the exact changes here for everyone's sake in the future.