The Outlook for Microsoft Outlook on the Mac is Good

Outlook icon

Outlook 2011 for the Mac is part of the Microsoft Office for Mac 2011 suite and is intended to replace Entourage 2008. The question here is, can it replace Apple’s Mail app?


For years, corporate customers complained that Entourage for the Mac was a crippled second cousin to Outlook for the PC. Corporate customers would complain to Apple, and Apple would gently and politely refer them to Microsoft. Behind the scenes, Apple would nudge Microsoft to listen to all the complaints and create an identical version for the Mac. Nothing happened. Nowadays, with the incredible popularity of the Mac, Microsoft has finally delivered Outlook for Leopard and Snow Leopard.

Review Focus

However, approaching this very capable e-mail program from the enterprise perspective isn’t the plan here. Many of the features are designed to work with a Microsoft Exchange server, and an assessment of that is better left to others. Instead, I’m going to approach the review from a different perspective.

Is this new e-mail program a worthy replacement for Apple’s Mail app?

Outlook Glamor

That’s an interesting question for me and, I think, many Apple customers because of the politics of e-mail programs. That is, as soon as the community’s technology agenda became to give away e-mail programs for free, almost all innovation evaporated from our e-mail clients. Eudora was dropped by Qualcomm because there was no money to be made in that atmosphere, and only a handful of minor e-mail programs stumbled on for the Mac. Except Entourage. And Entourage used a database that was susceptible to corruption which left a bad taste in the mouths of users and reviewers. Many Apple customers have used Apple’s Mail app as the least of all evils. Some have hungered for something more, including me.

What’s at issue here is an e-mail program that costs money and, in concert, takes e-mail seriously. Another way of saying that is that the app treats the user with respect. Of course, taking e-mail seriously doen’t mean that the app is perfect and all encompassing. Rather, I mean:

  • The app exhibits an understanding of how customers use e-mail, day to day.
  • The app has features that support the productive use of e-mail based on experience and research.

Microsoft, being a quintessential enterprise company, has many years experience with corporate customers and e-mail. So while I’m not reviewing Outlook 2011 from the perspective of the enterprise customer, Exchange Server, calendaring, meetings, and so on, the design of the app for those purposes requires a mature approach to the features and user interface. Basically, a lot of users, including me, appreciate that.

After all, there are small business users who still have to manage a lot of e-mail: writers, consultants, marketing specialists, independent travel agents, publicists, attorneys and so on. These kinds of users don’t appreciate an e-mail program that seems to condescend to non-technical users and whose updates are rare and seldom noteworthy.


Before I continue, I should point out some of the features and problems with Outlook 2011 so that, given what I’ve said above, you can steer clear if the app still doesn’t meet your needs. As a reminder, these pluses and minuses are with respect to the scope of this review.


  • Cocoa used for the UI, but some Carbon elements retained
  • Syncs with Mac OS X Address Book
  • Smart Folders
  • Filters and Search
  • Color coded categories and filter by category
  • Hierarchical message date presentation
  • The Ribbon
  • New e-mail storage system eliminates DB corruption, makes e-mail searchable by Spotlight
  • Unified inbox
  • Media Browser and attachment preview
  • Can import Windows .pst files and Apple mail
  • Built-in support for pane management, top to bottom or side by side
  • Supported by C-Command Software’s SpamSieve


  • Cannot sync with iCal, no CalDAV support
  • Project Center from Entourage is gone
  • Resend and Redirect commands from Entourage are gone

It’s the Little Things

Little things that exhibit a certain attitude about e-mail can be telling. For example, Apple has this concept of Smart Addresses. It’s a concept that, to me, suggests that Apple’s philosophy is that one has a few, informal friends for e-mail, so the name is displayed, but not the full e-mail address. Of course, one can turn this off in Viewing Preferences. In Outlook, one has to merely hover the cursor over the name to verify the full address. That can be really important in some circles to make sure you’re not sending sensitive information to the wrong person.

Outlook-3Full address popup on hover.

One feature I appreciated was the drawer on the bottom left: Mail, Calendar, Contacts, Tasks, Notes. If you need more room, drag the slider downwards and the text categories magically collapse, one by one, into icons. Little touches like that are impressive and helpful.

A look at the Ribbon in Outlook and the Toolbar in Apple mail reveals a very distinct difference in philosophy. Apple’s approach is to make e-mail fun, easy and approchable. Microsoft’s approach is to provide power and flexibility. This is a very clear choice that differentiates the two apps. If you never felt that Apple Mail has that Eudora-like power and control, you’ll probably appreciate Outlook.


The Ribbon is for power users.

General Use

Once you eliminate the differences in UI, philosophy and nuances, Apple Mail and Outlook are similar in functionality. Both have unified and individual account mailboxes, both have smart folders, both have auto-complete address fields, both do immediate spell checking and both have local folders that you can define.

However, Outlook has a slightly more sophisticated approach to viewing that uses a filter function. In the Mail app, the inbox is linear from the beginning, and your job is to use rules to delete or file messages into folders or smart folders. This can result in important messages being filed away and forgotten. In contrast, Outlook provides filters that can be additive for instant viewing. For example, display all messages that are unread and have attachments. Or, display all messages that have the category “family” — a category that was created, by a rule, when it arrived. It’s easy to undo these filters by unchecking the checkmark or clearing the filter. As a result, you can create a myriad of different kinds of inboxes that allow you to focus on the task at hand. Some have complained that each filter action doesn’t result in a new window, but I can see how that could result in too many open windows. Microsoft made a judgment call.


Filters and categories are easy, allow focus.

In Apple Mail, if you want to view the complete message header, you’ll have to go into Preferences and set a global, permanent setting. (Viewing -> Show header detail.) Then you’ll have to change it back when finished. In Outlook, on the other hand, you can just right click on a message and “View Source”. The output is directed to a text file for examination. Little things like this demonstrate that Microsoft gets what users need while Apple is stuck on the idea of enforcing simplicity to a fault.

Speaking of rules, Outlook has a very similar capability for invoking rules when messages arrive. The philosophy, however, has to be put in context. Apple’s mail app uses rules for disposition alone. Outlook, it seems to me, uses rules for not only disposition but also earmarking for later filtering and analysis. It’s a subtle but important distinction.

Outlook-6Actions for rules

I liked the way Outlook handles conversation threads. There’s a condensed view and an expanded view. In the condensed view, all the thread items don’t take up a lot of screen space. It’s easy to see which items in the conversation are unread. I also like the sound effects. While you can set your own sounds in the Mail app, the default sounds are so yesteryear. Outlook’s message sounds, believe it or not, are very classy.

I could go on at length about features in a one-by-one comparison, but that would run to another two thousand words and be tedious for all. (For example, certificates and encrypted e-mail. Importing from Apple Mail.) Instead, the goal has been to give you a feel for Outlook’s philosophy and design so that you can decide if you want to experiment and perhaps migrate away from the e-mail program you’ve been using. Because Outlook 2011 does away with the monster database approach, the risk associated with migration is greatly reduced.


There are several resources for the user.

I found the documentation to be readable and clear in every case I examined. Details are provided right down to the specific implementation and step-by-step instructions. Much is still a work in progress according to Microsoft, but it’s already terrific.

How to Get it

Outlook 2011 is included with Office for Mac 2011 Home and Business. It is not included with the Home and Student edition. What’s really annoying is that the app isn’t available for stand alone purchase. What this means is that for each individual who wants to use Outlook 2011, they’ll have to buy a copy of Office for Mac 2011*. Unless, of course, they’re benefiting from a site license from Microsoft. This is a shame because Outlook is a pretty good, stand alone e-mail client, and this policy will inhibit rather than promote its adoption by many potential customers.

Basic System Requirements

  • An Intel Mac
  • 1 GB of RAM or more
  • Mac OS X 10.5.8 or later
  • Display with 1280 x 800 or better resolution

Final Words

No e-mail app is perfect and no e-mail app will please everyone. For Apple enthusiasts who are accustomed to bashing Microsoft, especially Entourage, there will be an immediate, knee-jerk reaction that anything called “Outlook” is suspect. However, a closer inspection of the app reveals that Outlook 2011 has many good things to offer and will appeal to many users.

There’s a certain amount of comfort and safety associated with using Apple Mail. It’s free and simple. But for those who’ve never really been happy with Apple’s e-mail philosophy, including yours truly, this is a serious application that takes you and your e-mail seriously. In time, it’ll get better, but it’s a worthy 1.0 beginning.

Unfortunately, Microsoft has chosen to bundle it with Office for Mac 2011, and that will simply serve to insure that it never gets a chance to compete in the Apple community at large: Apple Mail, Eudora & successors, Mailsmith, Postbox, Thunderbird and so on. Maybe that’s the way Microsoft wants to keep it for now.

* I saw a two license version at Amazon. 

Product: Outlook 2011

Company: Microsoft

List Price: US$170 at Amazon (As part of Microsoft Office for Mac 2011 suite, Home & Business)



A mature, sensible, powerful and flexible approach to e-mail for personal or corporate use. Interfaces to Mac OS X Address book, allows user to window on date, filter, search and focus on e-mails of interest. Interfaces to iPhoto (Media Browser.) Uses QuickLook. E-mail storage modified to be Spotlight compatible. Rich sources of documentation.


No interface to iCal, CalDAV. Entourage’s Project Center, resend and redirect functions missing.  Available only with with Office for Mac 2011.