When Microsoft announced that they would build a Mac version of Outlook — their professional Windows email client — for Office 2011, I had some guarded hopes. After all, Encourage had proven to be a buggy mess. Not only would it crash frequently regardless of the Mac I was using, or the OS version, but that dreaded monolithic database file in which messages were stored might cause trouble.

You see, from time to time, the database would go bad. True, Microsoft had some clumsy tools to fix it, but unless you had a recent backup, no promises. Even with the backup, you might lose hours and hours of messages, critical ones.

Although it took a while for Apple’s Mail app to achieve a fair balance of features, performance, not to mention retaining a simple, elegant interface, it doesn’t seem as if Microsoft has made a whole lot of progress in building a robust email client. You’d think that, after spending tens of billions of dollars on research and development, surely there was enough cash left over to allow the Macintosh Business Unit the resources to give Office 2011 the proper level of spit and polish.

This doesn’t mean that Microsoft hasn’t done any updates to Outlook since the original release. There have been several, including one this week. But it seems as if most of the fixes dealt with potential security vulnerabilities and a few stability issues. But better stability doesn’t replace badly implemented features, or a curious behavior issue under Lion.

Now I realize Microsoft evidently expects to provide Lion compatibility in an Office update some time in 2012. So if you want support for such features as Auto Save and Version, prepare to wait. Or use iWork. But it’s also true that Outlook is unable to import user accounts from Mac OS 10.7 Mail. Is that also strictly a Lion compatibility issue? It would seem to me that parsing a few email settings for import ought to be a fairly trivial matter. But this is Microsoft, and nothing is trivial to them.

In any case, my experience with Outlook 11 was pretty awful on Day One, where I couldn’t get the app to run for more than a short time without seeing it unceremoniously quit. This usually occurred after configuring it with several email accounts, which have tens of thousands of messages. Since I use IMAP mail, all of these messages had to be downloaded from the mail server to my Mac, and that’s where things went astray. Maybe a memory leak? I don’t have the answers, except that a couple of updates later, that particular problem didn’t occur.

The next issue is rather more complicated, and if I lose you along the way in my efforts to make this clear to you, let me apologize in advance.

An email account will be divided into several folders, including the Inbox, Junk, Sent, Trash, Notes, and the folders you add to organize your messages. With an IMAP account, those messages will either appear as subdirectories of your Inbox, or separated from the Inbox under the email account name you specify. It’s a matter of preference, but Apple Mail will normally organize them separately, which is my preferred mode of operation. There is, in both Mail and Outlook, the option to collapse the Inbox, so all of the new mail seems to land in one place, though it’s actually still going to separate accounts.

Now in order for the email app to determine whether to integrate the other folders in your account as subdirectories of the Inbox, or to put them separately, you have to specify what’s called an IMAP Path Prefix in your preferences. In some email systems, it’s INBOX, in others it’s not necessary.

Now Apple Mail often figures this out in testing your account during the setup process, sometimes it doesn’t. But fixing the problem (or changing the layout) is simple and involves adding or removing the prefix, though it may take a few minutes for the app to reorganize loads of email.

Well, with Outlook 2001, the IMAP Path Prefix setting is meaningless. It doesn’t do anything, and thus the messages remain integrated with your Inbox in Outlook. You can’t change it, or I haven’t been able to do so. I’ve even posted a message in Microsoft’s support forum about the issue, and the support person who responded said there is no solution, at least for now.

I realize that such granular issues of email organization may not make very much sense to you, and thus you have no concerns about Outlook. I don’t think I’m alone in this concern, and that’s only part of the picture. I am not at all impressed with Outlook’s performance. Even though Microsoft has liberated the app from that monolithic database (there’s still a small one and the same awkward repair tools), performance remains tepid.

Microsoft insists that Outlook was built from the ground up in Apple’s Cocoa environment. Maybe so. But it sure does seem that a lot of bad coding concepts were carried through anyway, because Outlook doesn’t feel that much different from Entourage, except for the loss or alteration of some features, and the revised interface.

Maybe the Lion savvy version of Outlook will be better. But I’m not expecting much.

This article was posted on Thursday, December 15th, 2011 at 12:00 AM and is filed under News and tagged with: Apple, Apple Mail, Auto-Save, database, E-mail, Email Client, Imap, Inbox, Lion, Mac Os, Mac OS X Lion, Macintosh, Macintosh Business Unit, Mail, Microsoft, Microsoft Entourage, Microsoft Outlook, Office 2011, Outlook 2011.