The Outlook for Microsoft Outlook on the Mac is Good

| In-Depth Review

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?

Background

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.

Features

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.

Pluses

  • 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

Minuses

  • 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.

Outlook-4

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.

Outlook-5

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.

Documentation

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)

Pros:

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.

Cons:

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

The TMO Express Newsletter emails you the latest Apple headlines every weekday.

Comments

Tiger

Additional cons for Exchange users: YOU MUST BE USING Exchange 2008. 2003 is not supported. And considering the hefty MS license fees, it’s no wonder businesses and universities have stuck with 2003. Therefore, Outlook is not a viable option.

FlipFriddle

The real question is whether it’s finally feature-identical to it’s Windows version? That’s been the real crime with Entourage all these years; it could never really communicate with an Exchange server at the same level as Outlook for Windows and needlessly handicapped Mac users stuck in an Exchange environment.

No iCal support? To echo a common Bosco rant, “Where’s my choice?”

JonGl

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.

Shift-Command-H in Mail shows you complete headers, and no need to drop into Prefs. Also, no need to see the entire source of the msg, although if you wanted to see the raw source, there’s also Option-Command-U.

Also, looking at that ribbon, I’m not seeing what you are seeing. I see almost exactly the same sort of buttons that are available in Mail, with the exception of “Categorize” and a couple items that are also menu items, with keyboard shortcuts. Worse, the Outlook toolbar is uuuugly! I have to spend a fair amount of my time in my mail app. I got tired of looking at Entourage when i upgraded to OSX, so when Mail.app became usable around 10.3, I dumped it, and haven’t looked back. I had hopes that Outlook had learned how not to dress, but I see it hasn’t really learned much.

I do like those cascading filters, though…. I’ve wished for something like that.

-Jon

wab95

Many thanks for the thoughtful review, John.

There has been, as you are no doubt aware, a fair amount of chatter in the blogosphere about Outlook. The principal concern, and subject of negative comments, among reviewers at both Microsoft’s and Apple’s websites has had to do Outlook more than any other single feature of Office 2011 for the Mac. From my read, most of the adverse reaction is from recent Windows switchers intimately familiar with Outlook for Windows, who seem to feel that the Mac version is a hobbled, anaemic and gimped poor cousin to its Windows counterpart. Most of these users are probably also looking to use this in the enterprise workspace, but that is an assumption on my part.

As a former Outlook Express user, I at one point looked forward to a fuller version of Outlook for the Mac, as I do appreciate the Office package. However, similar to JonGI above, I have become accustomed to Mail in its increasingly robust iterations.

My principal issue with Outlook is that it is not CalDAV enabled, which beggars belief. I am now in search of solutions that allow for integration and harmonisation of my key data. A product that does not integrate with online calendar, or sync my calendars across devices, is not an option. Otherwise, I would have considered giving Outlook a spin.

brett_x

I like that they used a Mobius Strip for the “O” icon. That’s not as cool as when Apple used it for the base of the 17” Studio Display, but it’s not bad for Microsoft.

Lee Dronick

Shift-Command-H in Mail shows you complete headers, and no need to drop into Prefs. Also, no need to see the entire source of the msg, although if you wanted to see the raw source, there?s also Option-Command-U.

Thank you very much for those two tips.

DBS

“the Mac version is a hobbled, anaemic and gimped poor cousin to its Windows counterpart”

Exactly correct.

In its current state, Outlook for Mac is inferior to the old Entourage and no better than Apple Mail.

John C. Welch

Exchange 2003 is now seven years old, and the only protocol option for Outlook:Mac would have been HTTP-DAV, which gimped a lot of things in Entourage for years. Things like better exchange sync, etc.

Microsoft has gotten rid of HTTP-DAV in Ex2010, and they’re getting rid of MAPI in the next version of Exchange. Exchange is replacing HTTP-DAV *and* MAPI with Exchange web services. It would be stupid for Microsoft to target a dead protocol or even a dying one. it’s the same choice Apple made with Exchange support in Mac OS X 10.6. That’s EWS-only, so you have to use Ex2007 or newer. no 2003 support.

yeesh.

Sending from the drafts folder

Try sending a number of emails from the draft folder, select them all and hit command return!!!!

Its back to Entourage.

John Martellaro

Last post: give us more details, step by step, and I’ll ask Microsoft.
I went off line, composed some messages, then went back on line and they all were sent okay from the Outbox. But that’s probably different than what you did.

Sending from the drafts folder

Create a few emails, save them which places them in the drafts folder then select them all and hit command return, instead of them being sent to the outbox (as in Entourage) they all pop up and one has to send them individually.

Also a beef is the progress window which shows no information about what is coming in.

B9bot

Another big failure of Outlook 2011, no sync what so ever with any smart phones, including Blackberries and iPhones.
Why would MS leave out syncing of smart phones? Seems really dumb since most businesses want this especially when they’re on the go.
I guess they want to gouge the customer for there Exchange licenses another failure on MS.

John C. Welch

Another big failure of Outlook 2011, no sync what so ever with any smart phones, including Blackberries and iPhones.
Why would MS leave out syncing of smart phones? Seems really dumb since most businesses want this especially when they?re on the go.
I guess they want to gouge the customer for there Exchange licenses another failure on MS.

Microsoft hasn’t done direct sync conduits in *years*. Sync Services handles that, and the devices talk to sync services. This is not even VAGUELY new

PSMacintosh

John, you are doing us an injustice by comparing Outlook to just Mail because it infers that Outlook 2011 is a decent replacement for all of Entourage 2008.
Entourage 2008 has been besting the non-integrated Mail/Cal/Address Book combination for years.

Outlook 2011 does not even begin to replace Entourage.

Outlook is primarially a Mail Manager.
It’s fantastic that it has a new file system that will allow easier incremental backups.  (And I wish that Entourage had that.)

But Entourage 2008 is a much broader program with more extensive functionality.

Entourage handles 90% of my DAILY workflow. (Have to use Quicken for finances/bookkeeping and Safari for searches. Rarely have to use any other sw.)

Entourage does email.  But it also handles contacts, notes, projects, to dos, tasks, calendar.  It allows for extensive “categorization” and also excellent “linking” integration of all data/info.

I also use “contact” records to store other (non-people) type of information.  For example, I can keep “inventory” and “asset” info in a Contact.  (Could use a “note” but find that the “contact” record has more useful fields and the comment field can act as an internal note anyway, especially useful for communication logs.)

The LINKS are very powerful.  (Essentially there is a built-in database program within Entourage.)  I can add a Company as a contact, and then add and link Employee contacts to it. I can easily move between them.
When I buy software or products from a Company, I can create a “contact” record for each product I buy that is linked to the Company record. So I have info about the Company and then easy-to-locate info about its related employees and products.

You can LINK just about anything in Entourage 2008 (notes, contacts, cal events, tasks, etc) to anything else in Entourage. 
And, additionally, you can link to the other parts of the Office 2008 package that are outside of Entourage (to Word files, Excel files, and perhaps PowerPoint files).

And then there’s the built-in Project manager that already can automatically integrate/link with existing Contacts (and their Messages/Emails), Events, ToDos, Tasks.

All of this FUNCTIONALITY has been removed from the new Office 2011 and its meager Outlook 2011.

John C. Welch

Entourage does email.? But it also handles contacts, notes, projects, to dos, tasks, calendar.? It allows for extensive ?categorization? and also excellent ?linking? integration of all data/info.

Out of all that, Outlook doesn’t do exactly two things: Projects and linking.

I also use ?contact? records to store other (non-people) type of information.? For example, I can keep ?inventory? and ?asset? info in a Contact.? (Could use a ?note? but find that the ?contact? record has more useful fields and the comment field can act as an internal note anyway, especially useful for communication logs.)

Have you actually directly compared Outlook and Entourage’s contacts? Because you can do all of that in Outlook.

The LINKS are very powerful.? (Essentially there is a built-in database program within Entourage.)? I can add a Company as a contact, and then add and link Employee contacts to it. I can easily move between them.
When I buy software or products from a Company, I can create a ?contact? record for each product I buy that is linked to the Company record. So I have info about the Company and then easy-to-locate info about its related employees and products.

Links were powerful, but also, not a really top-used feature. But, doesn’t mean they can’t come back. You should perhaps tell Microsoft that this is important to you.

All of this FUNCTIONALITY has been removed from the new Office 2011 and its meager Outlook 2011.

You know, when you list a bunch of things, and then only two are missing, it kind of kills the meme that Outlook is OMG CRIPPLED compared to Entourage.

PSMacintosh

PSMacintosh said:Entourage does email.  But it also handles contacts, notes, projects, to dos, tasks, calendar.  It allows for extensive ?categorization? and also excellent ?linking? integration of all data/info.
Out of all that, Outlook doesn?t do exactly two things: Projects and linking.

Well that’s good to know.  Thanks.
Wonder why John M’s article only compared Outlook to Mail (versus comparing Outlook to the combo of Mail/Cal/Address Book/Text Edit/etc.)?  Oh, well.  Had me fooled (since I don’t have Outlook 2011).

John W, 
BTW, I enjoyed you excellent and useful review of Outlook 2011 at:
http://www.macworld.com/reviews/product/671493/review/outlook_for_mac_2011.html

I can probably get around not having Links and live without Projects.

I’ve not been using Time Machine because of Entourage’s file system (1 database structure), so I’d like to make the change.

Lauren

If you are going to purchase the student version you can buy it though the microsoft education store all you have to have is a valid email ending with .edu and then you are eligable to purchase the academic version of office 2011 and it includes outlook and a few other things then the home and student version

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