The first thing you notice is that, compared to the somewhat gray and sober Entourage ( ), Outlook 2011 is far cheerier and more colorful, and uses many more of the Mac’s familiar design conventions. Microsoft’s coders seem to have done an admirable job of packing Outlook’s mind-boggling abundance of features into a clear, coherent interface. For example, in each of Outlook’s five main panes (Mail, Calendar, Contacts, Tasks, and Notes), the new Ribbon interface runs across the top of the window, displaying sets of big, easily understandable buttons for the most important tools, grouped by tabs.
Outlook supports POP, IMAP, and Exchange accounts. In my first, quick tests, it handled all three without a hiccup. I couldn’t connect to a remote Exchange 2003 server, even over a VPN (virtual private network); I wasn’t able to determine whether this was Outlook’s failing, or some flaw in the server’s configuration. However, when I tried linking Outlook to an Exchange 2010 server instead, it connected instantly, and subsequently let me access all my mail, folders, calendar items, and reminders, even when I wasn’t connected via VPN.
Get it together
Two of Outlook’s biggest new features aim to help you tame your unruly inbox. First, you can now consolidate multiple accounts into a single Inbox (a feature available for a long time from rival Apple Mail [ ]). In my tests, this feature worked exactly as advertised; if you prefer to keep your accounts separate, you can turn it off.
Second, Outlook can display multiple messages from a thread under a single header. Grouping these related messages together helps keep them organized, but I wish the feature went one step further. When you click on a thread’s header, you can see the subject lines of all subsequent messages within the thread, but you can’t expand those messages to read more than one at a time. You have to click to display a single message, and then either click back to the overall list, or use the arrow keys to navigate to previous or subsequent messages.
In Outlook 2011, your daily list of upcoming tasks and appointments is presented in a separate application, My Day. (In the PC version, this is part of the main Outlook window.) This could be both help and hindrance. When you’re in Outlook, it’d be more convenient to have that information always visible, rather than floating around as another app. However, when Outlook is closed, that separation could be a good thing, allowing you to keep track of events without running the whole app.
Return to sender
Outlook 2011 also touts tighter integration with the Mac operating system; in my preliminary hands-on, it didn’t quite live up to those promises. The Quick Look integration works great, letting you preview e-mail attachments with a tap of the spacebar. However, the Time Machine support is more complex than Microsoft makes it sound. Unlike with Apple Mail, you can’t browse for older messages backed up with Time Machine from within Outlook. You have to use the Finder instead. That can mean digging through a baffling maze of nested folders in your Documents folder. (Mine went a whopping nine layers deep.)
I found Outlook’s importing features hit-or-miss. Address Book integration is superb, automatically syncing all your contacts, and even reflecting changes made within the Mac’s Address Book on the fly. You can also import mail messages from Apple Mail and other clients; but in my multiple attempts, not all of my messages made it over. Outlook faithfully duplicated my folders from Mail, but in my inbox, it imported only messages from one of my two Mail accounts, even though messages from the absent account showed up just fine in my other imported folders. According to Microsoft, this is a known bug, but there’s not yet a schedule for when it might be fixed.
In addition, Outlook won’t automatically import your iCal data into its calendar. You’ll have to export that information from iCal, and then import the resulting file manually.
Elegant finishing touches
Despite these hiccups, Outlook 2011’s many useful business-oriented features seem impressive. You can tell your calendar when your workday begins and ends, and import not only U.S. holidays, but also common holidays from dozens of countries all over the world—a clever addition for folks doing business internationally.
You can also create delegates and control their access to the various parts of your account. If your co-worker needs to share your messages about the project you’re both working on, and your assistant needs to add appointments to your calendar, you can allow them to do so without compromising the privacy of your entire account. You can even create multiple identities (one for work, and one for personal use, for example), although switching between them is a convoluted chore requiring a separate program, the Microsoft Database Utility.
In sum, Outlook appears to be a fine replacement for Entourage. We’ll take a closer look at it, especially its features for business use, in our full review.
Nathan Alderman is a writer, editor, and occasional meeting-misser in Alexandria, Va.