Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, predecessor to Entourage 2008 and part of the Office for Mac 2011 suite.

Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, not just an upgrade to its predecessor, Entourage 2008. Outlook 2011 has some features that Entourage had, but if you approach Outlook 2011 expecting it to be an upgraded Entourage, you’re going to be frustrated.

As someone who is, by any measure of the term, an Entourage power user, I found that once I stopped thinking about Microsoft Outlook 2011 as 'Entourage 2011', my experience with the new software quickly became much easier.

Version 1.0

Microsoft Outlook 2011’s Mailing List Manager, Scheduling Manager, and Rules implementation are mostly unchanged from Entourage. Otherwise, Outlook 2011 is all new. Anyone used to modern versions of Outlook on the PC, or for anyone on a Mac who needs to talk to Exchange, will find that Outlook 2011 will be kinder to you than Entourage ever was - as long as you're using Exchange Server 2007 or later. Outlook 2011 does not support the older HTTP-DAV connection method that Entourage used.

Microsoft Outlook 2011 is a Cocoa application; it doesn’t have a legacy of over 20-plus years on the Mac and doesn’t have the kind of code base that the other Office programs have. Moving forward, the Outlook development team will have an easier time than the other Office development teams with operating system compatibility. Unlike the rest of the Office 2011 suite, Outlook 2011 supports Mac OS Services (so did Entourage), and you get some of the basic niceties that Cocoa has.

Although I did no benchmark testing, Microsoft Outlook 2011 feels faster than Entourage. Outlook 2011 launches minutes faster for me on the first launch of the day after a shutdown. Some of the user interface (UI) lags in Entourage while checking mail or doing other tasks never appeared or were far less annoying than in Entourage.

Cocoa magic aside, drag-and-drop in Carbon applications always works more intuitively. As a result, Outlook 2011 takes a step back when it comes to drag and drop. You don’t have to do the click-and-hold delay when dragging text, and dragging an attachment into a background Entourage mail window is a far simpler experience than doing so with Outlook 2011, where I had to bring the message window to the foreground and then drag the file from a Finder window in the background to the message window. I’ve seen the same behaviour in other Cocoa applications - Cocoa just doesn’t do drag and drop as well as Carbon.

I tested Microsoft Outlook 2011 in the same configuration that I use Entourage on a daily basis: six IMAP accounts total, with three accounts using SSL for both send and receive, two Gmail accounts, and one Exchange 2007 Exchange Web Services (EWS) account. Back-end servers run the gamut from MobileMe, Kerio, and Communigate Pro to Exchange 2007. I have over 70 IMAP rules, a handful of SMTP and Exchange rules, and too many Mailing List Manager rules to count. I also have an Exchange Calendar with gobs of public folders (I live by my to-do lists), and I have three separate Directory Service accounts that I use as part of my work.

Microsoft Outlook 2011: the database

Entourage's database was a big file that changed constantly, which made for painful backups. The big news in Microsoft Outlook 2011 is that there is a new way of dealing with Outlook items, and each item is stored as an individual file or files - however, there’s still a database.

According to the Outlook development team, the database is there purely to optimise search and other non-essential routines. So what would happen if I deleted the database? After quitting Microsoft Outlook 2011 and the Database Daemon process, I deleted the database file and restarted Outlook 2011. The program popped a message saying that since I had restored from Time Machine, (amusingly, this message is hardcoded into Outlook 2011 based on the assumption that the only time you’re going to have all the individual files and no database is after a Time Machine restore), it was going to rebuild the database, which it did. The database is not only non-critical, it's much smaller; in my case, my Entourage Database is under 5.5GB, and my Outlook 2011 database is over 500MB. Not a bad reduction, and you can ignore it completely for backups.

Time Machine support is a mixed bag. Because everything is in individual files, once you’ve done your initial backup, then any changes only require backing up those changes, (just make sure you exclude the Microsoft Outlook 2011 database from Time Machine.) However, there’s no actual Time Machine integration,. And due to the requirements of Spotlight and others, the deeper folder structure is incomprehensible. For example, to get to my signatures, the folder path is /Volumes/jwelch/Documents/Microsoft User Data/Office 2011 Identities/Main Identity/Data Records/Signatures/0T/0B/0M/0K - not the things easy selective restores are made of.

The Outlook development team acknowledged that doing a partial restore, such as a single message or a single contact, would be quite tedious. In this release of Outlook, the restore is all or nothing, but a lot better than the state of Time Machine with Entourage. For anyone in a business or educational setting, where you’re using Portable Home Directory (PHD) sync, I noticed no problems with PHD sync at all. In a quick comparison, the synchronisation works as it does for Apple Mail as long as you exclude the Microsoft Outlook 2011 database.

Bringing in data from Entourage was a snap. Accounts, rules, signatures, e-mail, events, contacts, categories, and so forth, all imported without a problem on the first try. Importing from other programs was similarly pain-free. I also tried dragging a few thousand messages that existed only as .eml files into a folder in Microsoft Outlook 2011; it took a while, but they all imported correctly. The only caveat about importing is that if the Entourage Database Daemon is not running, the Entourage import may fail. I did not test .pst file imports.

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