Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, predecessor to Entourage 2008 and part of the Office for Mac 2011 suite.

Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, not just an upgrade to its predecessor, Entourage 2008. Outlook 2011 has some features that Entourage had, but if you approach Outlook 2011 expecting it to be an upgraded Entourage, you’re going to be frustrated.

As someone who is, by any measure of the term, an Entourage power user, I found that once I stopped thinking about Microsoft Outlook 2011 as 'Entourage 2011', my experience with the new software quickly became much easier.

Version 1.0

Microsoft Outlook 2011’s Mailing List Manager, Scheduling Manager, and Rules implementation are mostly unchanged from Entourage. Otherwise, Outlook 2011 is all new. Anyone used to modern versions of Outlook on the PC, or for anyone on a Mac who needs to talk to Exchange, will find that Outlook 2011 will be kinder to you than Entourage ever was - as long as you're using Exchange Server 2007 or later. Outlook 2011 does not support the older HTTP-DAV connection method that Entourage used.

Microsoft Outlook 2011 is a Cocoa application; it doesn’t have a legacy of over 20-plus years on the Mac and doesn’t have the kind of code base that the other Office programs have. Moving forward, the Outlook development team will have an easier time than the other Office development teams with operating system compatibility. Unlike the rest of the Office 2011 suite, Outlook 2011 supports Mac OS Services (so did Entourage), and you get some of the basic niceties that Cocoa has.

Although I did no benchmark testing, Microsoft Outlook 2011 feels faster than Entourage. Outlook 2011 launches minutes faster for me on the first launch of the day after a shutdown. Some of the user interface (UI) lags in Entourage while checking mail or doing other tasks never appeared or were far less annoying than in Entourage.

Cocoa magic aside, drag-and-drop in Carbon applications always works more intuitively. As a result, Outlook 2011 takes a step back when it comes to drag and drop. You don’t have to do the click-and-hold delay when dragging text, and dragging an attachment into a background Entourage mail window is a far simpler experience than doing so with Outlook 2011, where I had to bring the message window to the foreground and then drag the file from a Finder window in the background to the message window. I’ve seen the same behaviour in other Cocoa applications - Cocoa just doesn’t do drag and drop as well as Carbon.

I tested Microsoft Outlook 2011 in the same configuration that I use Entourage on a daily basis: six IMAP accounts total, with three accounts using SSL for both send and receive, two Gmail accounts, and one Exchange 2007 Exchange Web Services (EWS) account. Back-end servers run the gamut from MobileMe, Kerio, and Communigate Pro to Exchange 2007. I have over 70 IMAP rules, a handful of SMTP and Exchange rules, and too many Mailing List Manager rules to count. I also have an Exchange Calendar with gobs of public folders (I live by my to-do lists), and I have three separate Directory Service accounts that I use as part of my work.

Microsoft Outlook 2011: the database

Entourage's database was a big file that changed constantly, which made for painful backups. The big news in Microsoft Outlook 2011 is that there is a new way of dealing with Outlook items, and each item is stored as an individual file or files - however, there’s still a database.

According to the Outlook development team, the database is there purely to optimise search and other non-essential routines. So what would happen if I deleted the database? After quitting Microsoft Outlook 2011 and the Database Daemon process, I deleted the database file and restarted Outlook 2011. The program popped a message saying that since I had restored from Time Machine, (amusingly, this message is hardcoded into Outlook 2011 based on the assumption that the only time you’re going to have all the individual files and no database is after a Time Machine restore), it was going to rebuild the database, which it did. The database is not only non-critical, it's much smaller; in my case, my Entourage Database is under 5.5GB, and my Outlook 2011 database is over 500MB. Not a bad reduction, and you can ignore it completely for backups.

Time Machine support is a mixed bag. Because everything is in individual files, once you’ve done your initial backup, then any changes only require backing up those changes, (just make sure you exclude the Microsoft Outlook 2011 database from Time Machine.) However, there’s no actual Time Machine integration,. And due to the requirements of Spotlight and others, the deeper folder structure is incomprehensible. For example, to get to my signatures, the folder path is /Volumes/jwelch/Documents/Microsoft User Data/Office 2011 Identities/Main Identity/Data Records/Signatures/0T/0B/0M/0K - not the things easy selective restores are made of.

The Outlook development team acknowledged that doing a partial restore, such as a single message or a single contact, would be quite tedious. In this release of Outlook, the restore is all or nothing, but a lot better than the state of Time Machine with Entourage. For anyone in a business or educational setting, where you’re using Portable Home Directory (PHD) sync, I noticed no problems with PHD sync at all. In a quick comparison, the synchronisation works as it does for Apple Mail as long as you exclude the Microsoft Outlook 2011 database.

Bringing in data from Entourage was a snap. Accounts, rules, signatures, e-mail, events, contacts, categories, and so forth, all imported without a problem on the first try. Importing from other programs was similarly pain-free. I also tried dragging a few thousand messages that existed only as .eml files into a folder in Microsoft Outlook 2011; it took a while, but they all imported correctly. The only caveat about importing is that if the Entourage Database Daemon is not running, the Entourage import may fail. I did not test .pst file imports.

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Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, predecessor to Entourage 2008 and part of the Office for Mac 2011 suite.

Microsoft Outlook 2011: Email

I’m pleased to say that IMAP/SMTP accounts worked correctly in my testing. Microsoft Outlook 2011 handled both SSL and non-SSL accounts with ease, and HTML and plain text e-mails worked fine. Account setup is similar to the way it was in Entourage, except that the account settings have been merged into an all-new application preferences dialog box. The only glitch I noticed is that when you tell Outlook 2011 to use SSL with your SMTP account, it leaves the port at 25, instead of changing it to 465 - minor, but annoying. If you have an account with a mail provider Outlook 2011 knows about (like MobileMe), then the software does a good job of automatically setting up the account details.

One feature that's still missing from Microsoft Outlook 2011 is support for Kerberos as an authentication mechanism for IMAP/SMTP accounts. It’s available for Exchange, but the lack of Kerberos support means that you can’t use Single Signon for IMAP in Outlook 2011 as you can with Mail.

Another quibble is that the default compose setting can’t be set per account, so you can’t have one account that defaults to HTML and another that defaults to plain text. It’s a power feature and the Outlook development team said that it wasn't able to add it to the initial release. Other power features that are missing from Microsoft Outlook 2011 are the ability to add custom headers to e-mail messages, and the option to view the full headers of a message.

Gratifyingly, Microsoft Outlook 2011 continues Entourage’s limited support for HTML email. You can set basic options, such as font, font style, lists, indents and alignment, but no flashing text or tables. If you were expecting a full-on HTML editor, it’s not happening in Outlook 2011. However, Outlook 2011 is better at handling received e-mail than Entourage, which had a tendency to do bad things to HTML email when you forwarded it. Outlook 2011 finally lets you insert proper hyperlinks into an HTML message, something that Entourage couldn’t do unless you used Word as your editor. (I didn’t test to see if Word 2011 can be used as your email editor.)

For attachments, Microsoft Outlook 2011 can use Mac OS X’s Quick Look function to easily preview the attachment contents. While Outlook 2011 does have an updated junk mail filter, it’s still the same kind of filter as that in Entourage. It also seems to be unclear on the concept of “If someone is in my address book, then their messages aren’t junk” - I got inconsistent results.
The ability to reply to a message as a meeting is handy, although unless you’re running Exchange, you lose the ability to use the scheduling assistant to check availability. In my tests while running Exchange, this Microsoft Outlook 2011 feature worked flawlessly.

The UI for managing IMAP folders has changed quite a bit. It’s actually part of the new Public Folders window, and this is where you now manage subscriptions to IMAP folders. Unfortunately, all you can do with this new UI is subscribe or unsubscribe to folders. There’s no way to get any of the properties of that folder, or share the folder (Microsoft Outlook 2011 doesn’t support IMAP folder sharing), or even create a new folder here. You can create a new folder in the main mail view, but to have that option be only available for Exchange Public Folders in this window is frustrating, and hopefully this will change in a future update.

Microsoft Outlook 2011: Calendar

Microsoft Outlook 20011’s calendar contains some notable improvements on that in Entourage, such as better event displays, the ability to create multiple calendars (categories are still available), and more.

If you have multiple calendars, then Microsoft Outlook 2011 by default shows you a merged view for all calendars, local and Exchange. You can turn individual calendars on and off with ease. Categories are common across all calendars; there’s no way to have separate categories for each calendar.

One thing Microsoft Outlook 2011 does that iCal could take a cue from is that if you have a specific calendar selected, the events for all other calendars fade out a bit. It’s a small feature, but very helpful when trying to keep track your calendars. By default, all calendars have the same colour; if you want events to have different colors, you have to assign a category. One trick Outlook 2011 could stand to learn from iCal is the ability to change the calendar for an event from within the event itself.

Setting up events has changed a bit in Microsoft Outlook 2011. There are now two different kinds of events: appointments and meetings. The difference? You invite people to meetings, not to appointments. This separation is a bit pedantic, since you can invite someone to an appointment, but when you do, it changes itself to a meeting. Do you really need two buttons for what is really the same UI? I’ll hazard that this is one of those 'Outlook on Windows does this, so shall we' issues. It’s not evil, just tedious.

As part of the Ribbon UI change (I’ll specifically address the Ribbon later), there’s some handy controls added to Microsoft Outlook 2011’s calendar, such as dynamic resizing of your calendar view if you’re viewing your calendar as a grid, in Day, Work Week or Week mode. There’s no resizing for month other than resizing the window.

Microsoft Outlook 2011 has no CalDAV support. There are reasons for leaving it out of the first release (this version was heavily focused on Exchange), I hope future updates add CalDAV support—Outlook 2011 is entirely too useful to be solely bound to Exchange calendaring. You can use .ics files, but it’s not the same.

There’s also no Sync Services support for Events, so you can’t have Microsoft Outlook 2011 talk to iCal that way. The Outlook team stated this was due to the complications in syncing events in a transparent manner, and so rather than ship with the same kinds of problems that marred Entourage’s Sync Services implementation, they decided to wait until they could guarantee better results. Microsoft plans to add calendar sync support in a future update.

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Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, predecessor to Entourage 2008 and part of the Office for Mac 2011 suite.

Microsoft Outlook 2011: Contacts

Contact management stays much the same, with any changes in the UI being more for the benefit of Outlook/Exchange than anything else. If you’re using Microsoft Outlook 2011 with LDAP directory services, you can’t browse those directories, but the search works well. One complaint here is that Outlook 2011 assumes all directories are Active Directory (AD). If you’re using, say, Apple’s Open Directory, some things don’t show up correctly. Data like supervisor/supervisee information don’t show up if you aren’t using Exchange/AD, and you get an incorrect error message for that screen that there’s no directory service available - there is a directory service, just not AD. Providing directory/LDAP mapping information would be helpful in allowing system administrators to work around some of these issues.

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, Microsoft 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.)

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, Microsoft 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 Microsoft 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.

Microsoft Outlook 2011: 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 Microsoft 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 Microsoft Outlook 2011, 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.

Microsoft Outlook 2011: AppleScript

Outlook’s AppleScript support has been almost completely revamped and reorganised, 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, Microsoft Outlook 2011 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 in Microsoft Outlook 2011.

On the upside, there’s now a Debug suite for Microsoft 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 down side for me is the elimination of the 'part' element for email messages. In Entourage, this feature made it trivial to pull just the HTML or plain-text content from an email message. Without it in Microsoft Outlook 2011, you have to do a lot of parsing of the message source. That’s a problem for quite a few of my scripts.

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 Microsoft 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 Microsoft 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.

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Microsoft Outlook for Mac 2011 is a new email client and personal information manager from Microsoft, predecessor to Entourage 2008 and part of the Office for Mac 2011 suite.

Microsoft Outlook 2011: Exchange support

Overall, the Exchange support in Microsoft 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 Microsoft 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 Microsoft 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 Microsoft 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 Microsoft 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 Microsoft 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.

Microsoft Outlook 2011: The Ribbon

The Ribbon is a bit of a controversy. It’s a user interface element in all of the Microsoft Office 2011 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 Outlook 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 Microsoft 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 customisable, the Microsoft 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.

Microsoft Outlook 2011: Miscellaneous

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 Microsoft 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 Microsoft Outlook 2011, 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.

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Microsoft Office 2011 for Mac: Specs

  • Mac OS X 10.5.8 or later, Intel only
  • Mac OS X 10.5.8 or later, Intel only


Microsoft 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 behaviours 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.