For name recognition, it's hard to beat Microsoft Outlook. As soon as you say those two words, a large percentage of computer users immediately know what you're talking about. With the release of Microsoft Office for Mac2011, Microsoft rewrote the Apple Macintosh-based Microsoft Entourage email and calendar client and renamed it Outlook for Mac 2011. This change represents both a radical departure from previous versions of Entourage and Outlook's return to the Mac.

Years ago, Microsoft had an Outlook client for the Mac. That client used Messaging API (MAPI), but it was slow, buggy, not especially Mac-like, and feature-poor when compared with its Windows sibling. Microsoft replaced it with Entourage, and that was that. However, Entourage has long lacked many features that cross-platform users want, including compatibility with PST files, support for server-side rules, and numerous minor Outlook features. Outlook for Mac 2011 is Microsoft's attempt to bring its two Outlook clients closer to feature parity, as well as a competitive response against Apple's built-in email and calendar applications.

A Brief History of Outlook

The current version of Outlook for Mac is the direct descendant of Entourage, a personal information manager and email client that made its debut years ago in Office for Mac 2001. The original versions of Entourage used WWW Distributed Authoring and Versioning (WebDAV) for Microsoft Exchange Server support. When Microsoft announced that Microsoft Exchange Server 2010 would no longer support WebDAV, the Microsoft Macintosh Business Unit (known informally as MacBU) built a version of Entourage that used Exchange Web Services (EWS) instead of WebDAV. However, this change put companies with mixed Exchange Server 2003 and Exchange 2010 environments in a tough spot: Entourage 2008 Web Services Edition couldn't talk to Exchange 2003, and "regular" Entourage 2008 couldn't talk to Exchange 2010.

This situation continues with Outlook for Mac 2011, in that it supports only EWS as a means to talk to Exchange, limiting its use to Exchange 2007 and Exchange 2010. (The client also supports POP and IMAP for use with consumer services such as Windows Live Mail and Google Gmail.) However, Microsoft needed to rewrite much of the core Entourage code to make it more compatible with modern versions of Apple's OS and development tools. Outlook for Mac 2011 is the result.

It is reasonable to think of this Outlook client as a combination of the network core of Entourage 2008 Web Services Edition and a brand-new UI that attempts to blend elements of the Office 2010 Fluent User Interface (Microsoft's official name for the Ribbon) with Mac OS X. But the Ribbon-style UI isn't the only thing that's new in Outlook for Mac 2011:

  • A single unified Inbox view automatically collects messages from each account that you've configured. You can search, filter, and sort messages in their individual accounts or all in the primary Inbox view.
  • A new system for storing messages replaces the one monolithic database that Entourage used with individual message files. This approach is slightly less space-efficient but much easier for Apple's built-in Spotlight content indexing and Time Machine backup systems to handle. Plus, the new system eliminates the hassle of rebuilding corrupted Entourage databases.
  • This client provides support for reading and creating email that is protected with Active Directory Rights Management Services (AD RMS).
  • Outlook for Mac 2011 supports viewing and managing of server-side Exchange rules. (Entourage long supported client-side rules, and Outlook for Mac does as well.)
  • The client includes support for importing Windows Outlook PST files, although Outlook for Mac doesn't support the exporting of data to PST files. This feature alone caused a collective shout of joy in the Mac community, as the inability to deal with PST files has been a major hassle for mixed-OS organizations.

One of the much-touted new features of Office for Mac 2011 is its support for Visual Basic for Applications (VBA). The Office for Mac 2011 versions of Microsoft PowerPoint, Word, and Excel support VBA, but Outlook for Mac doesn't; you'll need to use AppleScript to automate and control Outlook. The AppleScript dictionary that is defined in Outlook for Mac 2011 differs in many respects from that of Entourage, so you should plan on spending some time testing and revising your Entourage scripts. In general, Outlook for Mac has more automation support than Entourage did, but some object types (notably public folders) aren't exposed in the dictionary and thus can't be automated.

Many other new features are less evident. For example, Outlook for Mac 2011 can update its account information after a cross-forest mailbox move, but you won't see that listed as a new feature and it isn't visible anywhere. Other semi-hidden features include support for federated calendar and free/busy sharing, as well as the ability to display the relevant portion of your calendar inline within a meeting-request message.

Perhaps the biggest feature in this category is the way in which Outlook for Mac 2011 stores messages. Entourage used one monolithic database to store messages, attachments, rules, and other metadata. If this database became corrupted, it needed to be rebuilt or restored -- often a time-consuming endeavor. For Exchange accounts, just throwing away a corrupted database and re-downloading messages from the server was generally no big deal, but in doing so you'd lose the local search index.

Having one large database also made it more difficult for Microsoft to integrate Entourage with the built-in Spotlight search system. To solve this problem, Outlook for Mac 2011 uses a much smaller database, and individual messages (and their message metadata) are stored in individual files. This arrangement eliminates the problem of data loss caused by database corruption and makes searching for Outlook content by using the built-in tools or system Spotlight mechanism gratifyingly quick.

A Quick Tour of the Outlook 2011 UI

Figure 1 shows the Outlook for Mac main window. If you've ever seen Outlook 2007 or Outlook 2010, this will be a familiar view. However, if you're used to Entourage, the appearance of the Ribbon might be a little confusing. At the top of the main window is an icon-only toolbar that gives you single-click access to commonly used commands. You can customize the commands that appear here. Immediately below this toolbar is a row of tabs: Home, Organize, and Tools. The contents of the Ribbon below these tabs change as you switch between them. Most of the commands here are directly equivalent to items that used to appear in the Entourage toolbar; as in Windows Office, some Ribbon icons are pull-down menus, as indicated by a downward-pointing triangle to the right of the icon.

Figure 1: Outlook for Mac 2011 main window
Figure 1: Outlook for Mac 2011 main window 

The same layout is used for message windows, although those windows have only one tab. The main Calendar, Contacts, and Tasks windows get the Ribbon treatment, as do the windows for individual items of each type.

Apart from the Ribbon, most of the UI changes in Outlook for Mac are fairly subtle. The UI retains the familiar three-column view, although there are some changes in the folder list that occupies the leftmost column. There's no way to reorder the accounts or folders that appear here, and Microsoft has decided to group them so that each account's related folders are together. For example, there's a single Drafts folder that shows you drafts from all defined accounts when selected. If you expand this folder, you see the individual Drafts folder for each account. After the grouped folders (Inbox, Drafts, Sent Items, and Deleted Items), separate per-account headings contain other folders, including the Conversation History and Sync Issues folders. Although this arrangement might seem a bit confusing at first, individual folders are accessible through the Inbox folder, just as they are in Outlook for Windows. This design parallels the approach that Apple took in its Mail application, so it's familiar to most Mac users.

Offline and Synchronization Behavior

One long-running irritation in Entourage was its synchronization behavior when used with Exchange. There was no way to control when or how it synchronized, and the Work Offline menu command often needed to be used to force disconnection and reconnection at unexpected times. Outlook for Mac's sync behavior is both considerably faster and much more robust than its predecessor. For example, when in offline mode, you're no longer prompted to go online and send the message each time you queue a message for sending. This prompt used to drive me absolutely crazy when working through email on long airplane flights.

However, there's no way to take an individual account offline or to provide separate sync settings for individual accounts. Outlook for Mac 2011 also lacks the extensive controls for dial-up and the low-bandwidth connection control that are included (though rarely used) in Outlook for Windows. In general, Outlook for Mac 2011 deals gracefully with changes or interruption in network connectivity, and it does so without any of the balloons or error messages that are familiar to Windows Outlook users. An activity window tells you which synchronization operations are in progress, but it doesn't contain much detail on which folders or messages are being synchronized at any given time.

Conversation Threading

Conversation threading is a semi-new feature in Outlook for Mac 2011 -- meaning that Entourage could sort messages by conversation, but only based on the text of the message subject. If you're accustomed to the way that conversation threading works in Outlook Web App (OWA) 2010 or Outlook 2010, then you might be somewhat disappointed by the Outlook for Mac 2011 implementation. The feature still depends on the message subject line and doesn't use the conversation headers that Exchange Server 2010 adds. So if your correspondents change the subject line of a message, the thread appears to break. This behavior is particularly annoying for threads that originate from systems such as Yahoo! Groups and Gmail, in which the mail transport system itself can (and often does) meddle with subject lines during normal operations.

Apart from that, there have been several bizarre bugs in conversation threading mode. One nice Outlook for Mac feature is the ability to switch to a view that shows only unread messages with a single keystroke (Cmd+Shift+O). However, in that mode, Outlook frequently loses track of how many messages are actually in a folder, and the selection behavior that is used to move between messages in a thread is often inconsistent. Almost all these bugs appear to have been fixed in Office for Mac 2011 Service Pack 2 (SP2).

What's Missing

There are two ways to categorize missing features in Outlook for Mac 2011: those which are present in Outlook 2010 for Windows and those that aren't. Microsoft never claimed that Outlook for Mac 2011 is, or is intended to be, a feature-for-feature clone of Outlook 2010. Instead, it tried to pick the most-demanded features from Outlook for Windows while still preserving a Mac-like experience that is well-integrated with the rest of the Office for Mac suite. Still, some Outlook 2010 capabilities would be welcome in a future release:

  • Support for an inline player for Exchange Unified Messaging (UM) voicemail messages -- Currently, UM messages appear as normal email messages with audio attachments; niceties such as the hyperlinks in Voice Mail Preview text that play the associated audio aren't supported. (Better yet would be if Outlook for Mac became a fully fledged UM client with support for Play on Phone and call-answering rules.)
  • Support for Outlook 2010 Quick Steps -- This handy feature quickly builds simple message-handling automation and binds it to a single keystroke or mouse click. Outlook for Mac includes a Scripts menu in which you can put your own AppleScripts, which can be bound to keyboard clicks. But having a single unified set of controls and behaviors across both sets of clients would be an improvement.
  • Support for displaying MailTips -- Entourage has long included the ability to display some metadata (e.g., "You replied to this message on...") in a MailTips-like interface, but Outlook for Mac doesn't consume the MailTips information that the Exchange Server 2010 content-addressed storage (CAS) exposes. This feature would be relatively simple to add.
  • ¬†Integration with the Exchange Personal Archive feature -- Several third-party archiving products integrate directly with Entourage and Outlook for Mac, although there might not be enough customer demand for this feature to make it worth implementing. Because Personal Archives are accessible through OWA 2010, Mac users still have full archive capability -- just not in the same client.
  • Voting buttons -- This commonly used Outlook for Windows feature still isn't supported on the Mac. This lack of support is a frequent complaint from cross-platform customers, but it's hard to gauge whether that's enough to warrant the development investment that would be required to implement this feature.

In the category of non-Windows Outlook features from which Outlook for Mac could benefit, the biggest is probably performance. Outlook for Mac sometimes feels ponderous when launching or switching modes; Apple's Mail.app feels much faster for many operations. In general, Outlook performance is significantly better than that of Entourage on similar hardware, but there are improvements yet to be made.

In a few areas, Outlook could be better integrated with Mac OS X and Apple's other apps, such as iPhoto (though there is a nifty new media browser for including iPhoto, iTunes, and iMovie content in messages), and there are certainly additional opportunities to integrate Exchange features. Overall, though, the missing features are minor when compared with the stability and functionality improvements that Outlook for Mac delivers.

A Bright Future

OWA 2010 is a fine client and is useful for a broad range of users. However, most users want a rich desktop client, and for Mac users in an Exchange environment, Outlook for Mac 2011 is it. None of the other available Mac OS X clients deliver the same combination of functionality and utility. Although the program has a few rough spots, Microsoft has fixed many of them in the first two service packs, and it's clear that Microsoft understands what Mac users with Exchange mailboxes want to see in a client. The future for Outlook on the Mac looks pretty bright.