There are still a lot of questions and tweets on Mac’s Outlook 2011, Exchange 2003 and why that combination doesn’t work. I can only assume people overlooked the system requirement in the Apple store, which clearly states “Exchange support in Outlook 2011 requires connectivity to Microsoft Exchange 2007 SP1 RU4 or later”.
The reason for lack of support lies in the fact that Outlook 2011 connects to Exchange Server using what is called Exchange Web Services. These services were introduced with Exchange 2007 (and thus are also available in Exchange 2010). The result is that Office 2011 can’t synchronize information, like e-mail, contacts and calendar, with Exchange 2003.
On a side note, you could use Entourage 2008 which utilizes the WebDAV protocol. This is supported by Exchange 2003 as well as 2007, but was discontinued in Exchange 2010.
Is this bad? I think not. Apart from the requirement, which is clearly mentioned, Exchange 2003 is almost 8 years old now. Products evolve and mainstream support has already ended for Exchange 2003. Even if Exchange 2003 is running rock solid, organizations should be considering on what to do with their Exchange 2003 environments as part of the IT life cycle management process.