Outlook to external exchange server not resolving server name

[Guest]

[unlearned]

Firstly the specs involved:

Appliance: Community
Version 3.0.devel
Kernel: 2.6.32.43-57.e51.i586

Internal Software
Windows 8 and Outlook 2013
WIndows 7 and Outlook 2010

External Server
Office365 business exchange server hosted by Microsoft

ISSUE:
  When adding a new account to outlook ANY or ALL of the following issues will occur
- When first setting up the account, no secure connection to server can be found.
- Connection found and popup asking for password keeps on popping up until it says 'exchange server is offline and cannot be found.
- Setup will complete successfully and outlook will restart (required restart) and the will ask for password repeatedly and then say 'Exchnage server cannot be found' or 'exchange server offline'.

Using a different router, all issues go away.

Have had the outbound firewall off and on, no difference
Have had transparent proxy on and off, when on, the above issues occur. When off the first issue ALWAYS occurs and no further steps can be done.

If I have missed anything please ask as I have literally spent 3 solid days scouring forums and google results to find a result before posting here.

[unlearned]

Anyone at all??

I have even done a clean install and it does not work...

At this point I wouldn't even but the paid version of Endian.