Although I’d much rather have Evolution or Thunderbird working with Exchange 2007, or perhaps even a new linux client that resembles the utility and usability of Outlook, I have to say Crossover Linux is a life-saver.  I’ve been working hard to obtain Exchange email/calendar/contacts via linux and the OpenChange/Exchange MAPI efforts just have developed well enough yet to use them.  Hopefully in the next 6 months the bugs will get worked out.

I attempted using Davmail, which has great potential if you can run it directly from or near your Exchange server, but I have no such option and the performance is abysmal.  Alas, I have resorted to running Outlook 2007 on Linux via Crossover.  The guys over at Codeweavers have done a great job with their Crossover suite — based on wine to enable Windows applications to run on UNIX/Linux-like systems as if they were native applications.

I’ve run into some issues along the way and resolving them has become quite a task.  Lets take it from the top:

  • Installing Office 2007 on Ubuntu Jaunty using Crossover 7.1 and Setting up Outlook to communicate with Exchange
  • Configuring additional email accounts (stunnel, crashes)
  • Outstanding issues (reloading of Inbox, inability to access POP/IMAP accounts without crashing or using stunnel — and still crashing)

Installing Office 2007

The first step was to get Office installed onto my ubuntu box.  This was fairly straightforward.  Install new windows application from the Crossover menu group.  Create the Windows XP bottle.  The first issue is that you have to connect directly to the exchange server (not to OWA using HTTP).  I installed the latest vpnc package since we use Cisco VPN.  Once connected, I could not get my account setup.  I kept getting an error indicating that I did not have a default gateway defined for my adapter.  This was true, but is also a bug of Outlook on Wine.  After some research, I came across this KB article on the Microsoft website:  http://support.microsoft.com/kb/913843.  This is a work-around for the default gateway issue and after applying it and restarting Outlook, I was on to finding my next issue!  I entered the required server and account information (I prefer defining the Exchange server settings manually as opposed to the discovery method).  Finally, my Exchange account was configured.

After some serious downtime waiting for the Inbox to “update”  I noticed a new issue:  Outlook disconnects from the exchange server very often.  It was at this point that I decided to give RPC over HTTP a whirl, and so I did.  This was _surprisingly_ simple.  I configured the settings, entered my owa URL, setup the authentication method, restarted Outlook and VOILA!  I disconnected from VPN and everything worked like a charm.  This was when I identified another, and still outstanding, issue.  Every time I restart Outlook, it attempts to “update” the Inbox.  Not just new messages, the ENTIRE Inbox, all 400mb.  I’ve yet to look at this issue any further due to other projects and work I’ve had going on.  Atleast Outlook is connected to Exchange and downloading email on Linux without a VPN connection.

Configuring additional email accounts

Now that Outlook is fetching my mail from exchange, its time to setup my other email accounts and see how that works out.  I configured my gmail account for POP/SMTP over SSL to no avail.  It absolutely would not download email or establish a connection for that matter.  I did some research and found out that this was just a problem that has not yet been worked out.  I decided there had to be a way to get this to work.  Not long after I came across this very informative post by Daniel Colquitt http://danielcolquitt.wordpress.com/2009/08/15/ssl-outlook-2007-crossover/.  Here, Daniel describes configuring and using stunnel to tunnel Outlook traffic over SSL to provide you a secure connection over the internet while allowing Outlook to run without utilizing any encryption.  I was able to connect and download my email!  Not so fast, problems on the horizon :(   I find that Outlook crashes very often with these accounts configured.  With that, and without time, I decided to disable stunnel and forego configuring my other email accounts on Outlook for now.

Outstanding Issues

Without time to troubleshoot, I’ve been unable to identify any solutions to the remaining problems:

  • Crashes while using POP or IMAP accounts
  • Re-downloading the entire Inbox after every restart

So that is where we stand until I can look into this further.  Hopefully I will have an update by the end of this week!  On to my VMWare Server installation.