Don't bother upgrading to Entourage 2008

If you're considering an upgrade to Entourage 2008, think again -- for some reason, Microsoft hasn't bothered to add some vital functions that are critical to making Apple Mac systems welcome on any Exchange network.

Entourage is basically a Mac-based version of Outlook and could be the application of choice for Apple users that need to collaborate with their Windows counterparts. However, after testing the latest version, Entourage 2008, it seems that compared to the previous version, the improvements are essentially cosmetic.

Ashwin Sridhar, technology manager at CNET Networks Australia -- the parent company of ZDNet.com.au -- manages a network of more than 60 machines in Sydney. A significant proportion of these system are Macs and Ashwin is responsible for making sure that users of both platforms can seamlessly collaborate with each other when it comes to calendaring and e-mail.

Having recently migrated the entire Australian operation to Microsoft Exchange, Ashwin had been looking forward to an Entourage update because users of the previous version were very vocal in their dislike of the older product (especially me).

After upgrading from Entourage 2004, the first thing he noticed was Entourage's new image, which isn't exactly revolutionary but does go some way to making it look more like a native Mac application -- instead of a Microsoft application invading the OS X desktop.

Unfortunately, that was about the only positive comment he had to make.

His biggest gripe was that Entourage 2008 still doesn't support the native Exchange protocol, instead it uses Outlook Web Access (OWA) to provide Exchange connectivity.

"Why Microsoft hasn't included native MAPI support in Entourage is a real mystery. Even Microsoft's own implementation of the OWA is lacking. Entourage 2008 still isn't able sync my To-do list with the Exchange server, which was a major failing in Entourage 2004. Third party applications such as Evolution seem to be able to perform this particular task just fine. The result is a set of tasks on my PDA to-do list won't sync with Entourage," said Ashwin.

The decision to have multiple search boxes was "puzzling", according to Ashwin. One search box is in the main toolbar, and the other, called Quick Filter, is located just above the listing pane for e-mail and contacts. On seeing two search boxes, Ashwin decided to hide the Quick Filter but then found that the search functionality had completely broken down.

"Typing in various combinations of search phrases and parameters failed to bring up either e-mail messages or the desired contact. It was not until a colleague reminded me of the Quick Filter that I was able to search through my e-mails and contacts again.

"Why have two search boxes when one of which doesn't yield any results?" he asked.

Ashwin was using the beta version of Office 2008 and the search malfunction has apparently been fixed in the retail version -- but there are still two search boxes.

Another major failing in Entourage 2004 that has not been addressed in the latest version, according to Ashwin, was that when e-mails are moved from the Exchange mailbox into a local folder -- or another mailbox -- they are not automatically deleted, which adds an unnecessary step.

"Go on, try it," he said. "Other mail clients -- including Evolution and Apple's own e-mail client (Mail) -- handle this task without issue.

"So it's back to moving messages and hitting the delete button for me," said an increasingly frustrated Ashwin.

Entourage also compromises usability for security -- the inability to include hyperlinks in e-mail signatures is a prime example, he said.

"HTML formatted e-mails usually look horrendous in Entourage, as the URL is displayed right next to the link. Moreover, clicking on links doesn't open them in the browser right away -- the application displays a dialog box warning the user that they have 'clicked on a link that might be a fraud'," said Ashwin.

Another complaint -- but a minor one -- is the MyDay feature, which has been touted as a major enhancement. According to Ashwin, Microsoft should have spent its development resources elsewhere.

After playing with Entourage 2008 for over a month and comparing its functionality to that of the previous version, I asked Ashwin if he thought upgrading to the latest Entourage (and therefore Office 2008) was worth the money.

His answer, unsurprisingly, was "no".

"Entourage 2008 is still plagued by the same old issues that made me hate its older version. For now, I'm going back to using Mail as my primary mail client with Entourage running in the background -- just for calendaring purposes.

"Perhaps the next version of Mac Office will fix these issues. I am not holding my breath," he shrugged, while walking back to the server room.

So why would Microsoft do such a bad job of "improving" Entourage 2008? If I was cynical, I would say it was to discourage companies from deploying anything but Windows on their network.

But Microsoft would never do that, would it?