Outlook 2010/2013 can't connect to Exchange 2007 via Outlook Anywhere

[mlbasso]

I recently have several users complaining they can no longer use Outlook (2010) from home. They open Outlook and it tries to load profile but fails after a few minutes. If you click retry it may or may not connect. Most users don't bother and switch to OWA. I normally VPN in so I never noticed. However, when I do not VPN in it does not work for me either(I'm using Outlook 2013). Outlook Anywhere is configured and had been working for years. I ran every test imaginable (ex.https://www.testexchangeconnectivity.com/) and each test succeeds. On my laptop, with Outlook connected while connected via VPN, I can disconnect VPN and Outlook will reconnect. I have another "old" windows 7 laptop with Outlook 2010 at home and it works fine. So it is not consistent. How do I go about troubleshooting this? thanks in advance.

[ZeroHour]

I am not sure if it would have affected you but there was an update released for Office 2013 (and 2010 I suspect) that was for O365 compatibility which broke non o365 (new wave) stuff.

If you have some time try removing office from your machine or fresh installing somewhere and dont update office first to see if it works then with a base install. I cant remember the KB for the update sadly but if you drop a list of available ones via windows update I may spot it. It may only have affected o365 users but it basically broke part of the auth process and o365 used outlook anywhere functionality.