I had been struggling with this for over a month. Finally a break-through today. Mind you this is still not official since I managed to get it working using a nightly build, not an official release. Steps as follows:
- Start with an installation of 14.1.4
- Install Office 2010 (Outlook 2010 and whatever else you need)
- Install Office 2010 SP1 (unless your install media includes it)
- Install the April 2012 Outlook update (KB2553248) from here: http://www.microsoft.com/en-gb/download/details.aspx?id=29361
- Upgrade to crossover nightly build 20150801
As it turns out, KB2553248 is needed to enable the so called "Anonymous Authentication" for "Logon Network Security". This is needed after changes to Exchange Online (so called Wave 14 to Wave 15 changes: http://blogs.msdn.com/b/scottos/archive/2013/07/25/outlook-can-t-connect-to-office-365.aspx).
Another quirk with recent wine releases (hence recent crossover versions) is that they leave .lnk files lying around everywhere if directory "~/.cxoffice/<Office 2010 bottle name>/drive_c/users/crossover/Recent" does not exist. These are generated to support the File -> Recent option in various Office applications (e.g. Word). If it doesn't exist, create it manually; all .lnk files will then be saved there instead of the current working directory.
Hope the above helps! Best,
Dimitri