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Outlook for Mac 2011 — Still Not Ready for Prime Time

So Microsoft has released some maintenance updates to the Office 2011 for Mac suite over the past few months. They were largely designed to patch security holes, or fix some bugs. For the most part, I’ve seen no change in Word or Outlook, and the latter remains a tough sell, in severe need of real change.

As for Word, I agree with the reviewers that it’s petty snappy for such a bloated beast. For me, it often launches faster than Apple’s Pages, but that’s another story. On the other hand, when you open a Word document, it wants to be pinned to the left side of the screen, even though you take efforts to center in on the screen before quitting. Well, I’m sure it’s not because the ability to pin document windows to the corners of the screen is touted as a major feature of Windows 7. Maybe Microsoft’s Mac Business Unit doesn’t believe that people care about the inability to remember a document window’s position between launches.

But my real beef remains with Outlook 2011, the replacement for the bug-ridden Entourage. Outlook is supposedly written from the ground up in Apple’s Cocoa programming environment, although it seems to behave in many ways similar to Entourage. It’s almost as if Microsoft just ported the code over, without actually changing it. Well, in some ways.

The similarities might, of course, be designed to make the app seem as familiar as possible to the existing user base. That way, you can readily absorb the changes without complaining. Would that Microsoft did the same on the Windows side of the ledger. In any case, basic setups in Outlook are essentially the same as Entourage. Unfortunately, it’s also incredibly flaky.

Let me give you an example that became particularly irritating.

Now those of you who used Entourage recall its Achilles heel, which was the questionable decision to store all of your messages in a monolithic database. If that database got corrupted, you had to confront the ever-present danger of losing some or all of your messages. Of course, if your email service uses IMAP, as mine does, you can just dump the database, and wait for the messages to be downloaded all over again.

Outlook does have a database, but actual messages are stored as separate files. This is designed to make the app more efficient, more easily backed up in Time Machine, and to help protect you from the slings and arrows of damaged databases. But that doesn’t mean it can’t screw up your messages.

Some weeks back, Microsoft released yet another service pack for Outlook. I was otherwise occupied, but decided to give it another try the other day. To be sure, I was starting from scratch as much as possible, I deleted all relevant preference files (including those in the Identities folder found in the Microsoft folder).

That should have meant a relatively clean experience. The mistake I made, I suppose, was to import all of my accounts from Apple Mail. The actual messages would be downloaded from the relevant servers, including the one we use for our sites, AOL, MobileMe, and Gmail.

Welcome to the world of scrambled eggs.

While actually downloading messages, and I have over 50,000 stored in various accounts and folders, Outlook became predictably sluggish. Anything I’d do doing this process would convey the feeling of slogging through quicksand. So in that respect, Outlook isn’t all that much speedier than the last version of Entourage.

As before, Outlook’s curious spam filter would take a few dozen old messages and suddenly deposit them in the various Junk folders in my accounts. That action was no different from Entourage, which merely conveyed a further impression of familiarity (with a little contempt for the process).

The real problem occurred, however, when Outlook decided play a game of scrambled eggs and deposit messages in the wrong folders. Yes, I’m serious! No, it wasn’t a problem with my email server, which has worked perfectly on all my computing devices, using Apple Mail and other email clients. What this meant was that messages earmarked for a folder in one account would end up in the folder of another account. Yes, I’m serious, and, again, this isn’t something that could be traced to the email server, which was otherwise totally reliable.

When the email downloads were done, I quit Outlook. Unfortunately, the app’s corruption of email locations was apparently uploaded back to my email server, so I spent the next few hours in Mail attempting to sort things out.

Yes, I realize some of you might blame the server and not Outlook, but the timing was awfully coincidental. More to the point, returning to Mail produced no more problems, no more messages being deposited in the wrong places.

Outlook has an attractive interface, and the Mac variation of Microsoft’s infamous ribbon toolbar scheme actually looks quite decent. Other than struggling to cope with multiple activities on a late 2009 iMac with quad-core processor and lots of RAM, I could get used to it. But it still needs serious work, and, even if there’s another update soon, I don’t know that I want to confront the possibility of having to reorganize my email all over again.