capsule review

Microsoft Outlook for Mac 2011

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My test results with Exchange were odd. I could not get contact searches to work with Exchange 2007 in the Contact view, although they did work correctly for e-mail and meeting lookups as long as you sent from an Exchange account. If you sent from a non-Exchange account, Outlook 2011 never was able to correctly do lookups in the Exchange Global Address List (GAL). While GAL browsing is enabled when used against Exchange 2010, I was unable to test this, as I used Exchange 2007 for this review. (It is entirely possible my GAL issues were due to a configuration problems. Because the GAL searches didn’t work only in the Contact view or from the search field on the Outlook Ribbon, it was probably a problem with my network setup, not with Outlook itself. However, Outlook’s error messages were of no help, something that could and should be enhanced in future updates.)

Search Contacts: During this review, contact searches using the Contact view didn't work with Exchange 2007.

LDAP searches were flawless and fast, faster than in Entourage. Searching for contacts is easier, although your options are limited to search names only, or search all fields. Simple, but a bit limited. As with Entourage, Outlook 2011 doesn’t display any picture for a contact from an LDAP directory, even if one is present. Maps are provided by Microsoft Bing.

As with CalDAV, there’s no CardDAV support, so you are unable to use Outlook 2011 with Apple’s Address Book server or any other CardDAV server. As with CalDAV support, I hope to see CardDAV support in a future release. There are a lot of businesses running on CalDAV, CardDAV, and IMAP, and Outlook 2011 could be a great option for them if it extends its open standards support to CalDAV and CardDAV. Contact syncing via Sync Services worked well, with no noticeable issues.

Notes, Tasks, To-Dos

There’s not a lot of changes here; not a lot needed to be changed. Tasks and Notes sync with Exchange, and you can use public Task and Notes folders on an Exchange server. You can create local folders for both tasks and notes. If you have flagged an IMAP message as a to-do in, say, Entourage, those to-dos will show up correctly in Outlook 2011.

Notes are extremely simplistic, which is fine. I did notice that although I can see the folder for Apple Mail To-Dos in Outlook, if I actually click on one, it shows up as a plain-text e-mail message with the warning that I am to do nothing to it, because it is managed by Mail. I was not able to see Mail’s notes.


Outlook’s AppleScript support has been almost completely revamped and reorganized, which leads to a mixed bag of results. Each major functional area has its own suite, including Tasks and Notes. There’s even a new Schedules suite. That’s nice, but there are a lot of changes that go along with this. For example, to get the selected message, you can no longer use “selection”; you have to use “current messages” or “selected objects.” Also, Outlook finally doesn’t add garbage characters on the end of HTML messages when you get the contents of an e-mail message.

There are a lot of things that are read-only that shouldn’t be, like message, contact, and task folders. It would also be nice if you could explicitly set the contents of a message to HTML, rather than having that be derived from the contents. There’s no easy way to move or copy messages between folders.

On the upside, there’s now a Debug suite for Outlook 2011 that lets you run a small number of tests, including junk score testing. Unfortunately, the way the debug suite is set up, you can only see it in Late Night Software’s Script Debugger, not the default AppleScript Editor. (It may also be visible in Smile, but I don’t use Smile.) I love Script Debugger, but the debug suite is something that should be available to any AppleScript tool.

A huge downside for me is the elimination of the “part” element for e-mail messages. In Entourage, this feature made it trivial to pull just the HTML or plain-text content from an e-mail message. Without it, you have to do a lot of parsing of the message source. That’s a problem for quite a few of my scripts.

AppleScript: Outlook 2011's implementation of AppleScript is a good start, but it has room for improvement.

The Outlook development team acknowledged these shortcomings and a few others, and said that they are working on an update that will fix a lot of AppleScript support. If you do use AppleScript with Entourage, I would recommend waiting until Outlook 2011’s AppleScript implementation gets the necessary fixes. It’s just too incomplete at the moment to really use. Once the holes are patched, I think this will be an amazing application to script.

Before we move on: there’s no VBA in Outlook 2011. If you were counting on it, sorry. But seeing what a pain it has been for Outlook on Windows over the years, I regard this as a good decision.

Exchange support

Overall, the Exchange support in Outlook 2011 has gotten some major love over Entourage, even with the improvements in Entourage 2008 Web Services Edition (EWS). (I’d like to reiterate that I only tested Outlook 2011 against Exchange 2007.) Things that took multiple steps in Entourage, or never seemed to work right, especially with regard to scheduling, just worked in Outlook 2011. I did have some bumps, such as my problem with searching the GAL, but I attribute that to my setup. I was on the other side of the United States from the Exchange server I tested with. My setup was almost a worse-case scenario, and it still worked well. Given a more standard setup, I see the few problems I ran into just going away.

I was impressed that with my setup, the autodiscover functionality for Exchange worked, and worked correctly. Since it was unable to detect a Kerberos KDC, it correctly defaulted to username and password authentication. Outlook 2011 finally fixes one huge Entourage annoyance: using Entourage with Exchange. If the connection to the Exchange server was interrupted, the only reliable way to get it back was to restart Entourage. That’s fixed in Outlook 2011.

You cannot set up Exchange Server Rules yet, but that is a limitation of EWS. Once the Exchange team updates EWS to allow that functionality, I’m pretty sure Outlook 2011 will also get it. Oh, and yes, Outlook only supports Exchange Web Services, so Exchange support is limited to Exchange 2007 and later. No Exchange 2003 or earlier, unless you’re using IMAP/SMTP.

That doesn’t mean you are locked into Exchange, or at least you won’t be for long. Kerio, makers of the Kerio Connect groupware server that runs on Mac OS X, Windows and Linux, recently announced that the next update to Kerio Connect, version 7.2 will have EWS support, and so will be able to support the Exchange functionality of Outlook 2011 (along with Entourage EWS and, presumably, the Exchange functionality in Mail, iCal, and Address Book). This is great news, as I run a Kerio Connect server, but it’s also great news for any company that doesn’t use Exchange but wants or needs that functionality. EWS support also greatly simplifies connecting Outlook on Windows to Kerio, since the old MAPI (Messaging Application Programming Interface) connector is no longer needed, just use EWS.

So Outlook 2011’s Exchange features will be of use to people not using Exchange as well, a win for all. One obvious note: Outlook 2011 is not a 100 percent feature-for-feature match with Outlook for Windows. It may never be, and I can think of a few things that would never be worth the effort to implement outside of Windows. But it is a solid improvement on Entourage, and I’ve no doubt it will continue to improve over time. Just keep your expectations realistic.

When comparing Outlook 2011 to Mail, iCal, and Address Book as an Exchange client, it’s no contest. Outlook wins, just as Entourage EWS won when I compared it to Snow Leopard’s Exchange integration. This should come as little surprise to everyone. Outlook 2011’s Exchange integration is at the heart of the program, indeed, improving that from Entourage EWS was a major requirement of Outlook’s development. In comparison, Snow Leopard’s Exchange integration is a convenience factor. It’s not designed to be a full-featured Exchange client, but to give you access to basic Exchange functionality for no additional cost. Just like Pages is a better word processor than TextEdit, Outlook 2011 is a better Exchange client than Mail, iCal, and Address Book.

The Ribbon

The Ribbon is a bit of a controversy. It’s a user interface element in all of the Office programs that sits at the top of the document window and provides quick access to the most commonly used tools. At first, because of my experience with Entourage, I hated it. I like to have a minimal UI. After using it for a while, I’ve changed my opinion. The Ribbon is a bit garish, but it does keep the options I use frequently right where I need them. It doesn’t get in the way and it takes up a minimal amount of space.

Every keyboard shortcut I used with Entourage works as expected with Outlook 2011, which made the UI changes far easier to deal with. Also, unlike what you see in Office for Windows, the full Mac Menu Bar and its structure are still there, so if you like, you can collapse the Ribbon and use the menus and key commands.

My biggest complaint is that unlike in Windows, where you have the Quick Access Toolbar that was highly customizable, the Outlook 2011 toolbar is almost vestigial. The only commands it can have are Send/Receive, Help, My Day, Print, Undo, Redo, and Search. Personally, I yanked everything but Search—all the others I do via key commands.


The My Day program that allows you to track your daily list of upcoming tasks and appointments gets an update as well. It picks up a bit more functionality, some resizing improvements, and a general theme change. It doesn’t do much, but that’s by design, and it is handy for keeping your upcoming appointments and tasks accessible when Outlook 2011 is not running. I did run into a really persistent bug where even on blank installs, with no migration from earlier accounts, My Day’s window just would not appear.

For users transitioning from Entourage, I had no problems with keeping both versions of the Database Daemon running, as due to the My Day "no window" bug, I had to use Entourage’s version of My Day. I used that with Outlook, and had no noticeable problems. I wouldn’t recommend keeping both Outlook and Entourage running simultaneously, but, for testing purposes, you can quickly switch between the two without having to remember to kill one or the other’s Database Daemons.

Macworld’s buying advice

Outlook 2011 is not a follow-on or new version of Entourage. It is a 1.0 program, that is a huge change from Entourage in almost every way. The number of Entourage behaviors preserved unchanged probably fit on the fingers of both hands, maybe with a toe or two. That’s neither bad nor good. It’s just different.

Outlook 2011 is different enough that Entourage users will have to make big adjustments. Users from current versions of Outlook for Windows will probably have the fewest issues. As a 1.0 product, there are a number of feature holes and bugs that need to be fixed and fixed quickly, but none were major inhibitors. If you need an Exchange client on the Mac, Outlook 2011 is the king. It’s not cheap (being part of Office 2011), and there’s no way to just buy Outlook 2011, but if you need Exchange, or just want something more than Mail, iCal, and Address Book give you, Outlook is a no-brainer. With Kerio’s upcoming support for EWS, Outlook won’t be as tied to Exchange as it currently is.

[John C. Welch is the IT Director for The Zimmerman Agency, and a longtime Mac IT pundit. Special thanks to Andrew Laurence and the Exchange team at the University of California, Irvine, for assisting John with this review.]

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At a Glance
  • Pros

    • New interface makes many tasks easier to access
    • Improved Exchange support
    • Faster than Entourage
    • Redesigned AppleScript dictionary
    • No longer reliant on a single database
    • Better support for Time Machine and Portable Home Directory Sync
    • Redesigned preferences make setting up the application easier
    • UI more compatible with Outlook on Windows


    • Assorted 1.0 bugs
    • AppleScript implementation holes mar improvements to AppleScript Dictionary
    • Exchange support requires Exchange Web Services
    • Exchange 2003 and earlier not supported
    • Exchange support limited to what EWS allows
    • Time Machine limitations
    • UI changes hardest on existing Entourage users
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