Outlook for Mac 2011 — Still Not Ready for Prime Time

February 11th, 2011

So Microsoft has released some maintenance updates to the Office 2011 for Mac suite over the past few months. They were largely designed to patch security holes, or fix some bugs. For the most part, I’ve seen no change in Word or Outlook, and the latter remains a tough sell, in severe need of real change.

As for Word, I agree with the reviewers that it’s petty snappy for such a bloated beast. For me, it often launches faster than Apple’s Pages, but that’s another story. On the other hand, when you open a Word document, it wants to be pinned to the left side of the screen, even though you take efforts to center in on the screen before quitting. Well, I’m sure it’s not because the ability to pin document windows to the corners of the screen is touted as a major feature of Windows 7. Maybe Microsoft’s Mac Business Unit doesn’t believe that people care about the inability to remember a document window’s position between launches.

But my real beef remains with Outlook 2011, the replacement for the bug-ridden Entourage. Outlook is supposedly written from the ground up in Apple’s Cocoa programming environment, although it seems to behave in many ways similar to Entourage. It’s almost as if Microsoft just ported the code over, without actually changing it. Well, in some ways.

The similarities might, of course, be designed to make the app seem as familiar as possible to the existing user base. That way, you can readily absorb the changes without complaining. Would that Microsoft did the same on the Windows side of the ledger. In any case, basic setups in Outlook are essentially the same as Entourage. Unfortunately, it’s also incredibly flaky.

Let me give you an example that became particularly irritating.

Now those of you who used Entourage recall its Achilles heel, which was the questionable decision to store all of your messages in a monolithic database. If that database got corrupted, you had to confront the ever-present danger of losing some or all of your messages. Of course, if your email service uses IMAP, as mine does, you can just dump the database, and wait for the messages to be downloaded all over again.

Outlook does have a database, but actual messages are stored as separate files. This is designed to make the app more efficient, more easily backed up in Time Machine, and to help protect you from the slings and arrows of damaged databases. But that doesn’t mean it can’t screw up your messages.

Some weeks back, Microsoft released yet another service pack for Outlook. I was otherwise occupied, but decided to give it another try the other day. To be sure, I was starting from scratch as much as possible, I deleted all relevant preference files (including those in the Identities folder found in the Microsoft folder).

That should have meant a relatively clean experience. The mistake I made, I suppose, was to import all of my accounts from Apple Mail. The actual messages would be downloaded from the relevant servers, including the one we use for our sites, AOL, MobileMe, and Gmail.

Welcome to the world of scrambled eggs.

While actually downloading messages, and I have over 50,000 stored in various accounts and folders, Outlook became predictably sluggish. Anything I’d do doing this process would convey the feeling of slogging through quicksand. So in that respect, Outlook isn’t all that much speedier than the last version of Entourage.

As before, Outlook’s curious spam filter would take a few dozen old messages and suddenly deposit them in the various Junk folders in my accounts. That action was no different from Entourage, which merely conveyed a further impression of familiarity (with a little contempt for the process).

The real problem occurred, however, when Outlook decided play a game of scrambled eggs and deposit messages in the wrong folders. Yes, I’m serious! No, it wasn’t a problem with my email server, which has worked perfectly on all my computing devices, using Apple Mail and other email clients. What this meant was that messages earmarked for a folder in one account would end up in the folder of another account. Yes, I’m serious, and, again, this isn’t something that could be traced to the email server, which was otherwise totally reliable.

When the email downloads were done, I quit Outlook. Unfortunately, the app’s corruption of email locations was apparently uploaded back to my email server, so I spent the next few hours in Mail attempting to sort things out.

Yes, I realize some of you might blame the server and not Outlook, but the timing was awfully coincidental. More to the point, returning to Mail produced no more problems, no more messages being deposited in the wrong places.

Outlook has an attractive interface, and the Mac variation of Microsoft’s infamous ribbon toolbar scheme actually looks quite decent. Other than struggling to cope with multiple activities on a late 2009 iMac with quad-core processor and lots of RAM, I could get used to it. But it still needs serious work, and, even if there’s another update soon, I don’t know that I want to confront the possibility of having to reorganize my email all over again.


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8 Responses to “Outlook for Mac 2011 — Still Not Ready for Prime Time”

  1. Andrew says:


    I’ve had a very different experience, though I use Microsoft Exchange rather than iMap, so that could be the reason.

    Like you, I have upwards of 50 or 60 thousand emails stored in a multitude of folders over the last 10 or 11 years. As an Exchange user, however, I’ve always used Outlook for Windows or Entourage until the arrival of Snow Leopard when Mail and iCal became an option. Even then, familiarity had me stay with Entourage over Mail/iCal, and I only made the move to Mail when I moved my calendars off of Exchange and onto Market Circle’s DayLite suite, relegating Exchange to email only.

    I liked Entourage 2008. Once the move was made to the Web Services Edition and my Exchange server upgraded from Exchange 2003 to 2007 I found email to be fast, smooth and reliable enough that I could ditch WIndows clients completely in my office and go 100% Mac (except for the Exchange server itself). Once that server reaches age 3 (half way there) I will replace it with a Mac Mini Server and be completely OS X, but that is another story.

    Outlook 2011 had some very annoying bugs when it arrived, though as an Exchange user the bugs I experienced were different than those you describe, mostly relating to the application freezing for up to a minute at a time on selecting a message. Microsoft fixed that issue in the first update. There was another issue relating to stability on imported Entourage identities, which apparently was fixed as well, though I had already worked around it by creating my identity from scratch, which is easy with an Exchange account.

    Today I am back to using Apple Mail for my business Exchange account, but I still use Outlook for my personal Exchange account. I prefer Outlook. Its message writing tools are far more robust and it handles attachments in a way that displays cleaner. Most of it is familiarity, I’m sure, as I’ve used Outlook for Windows and Entourage for Mac since 1997, and only use Mail now for work because of its integration with DayLite. If DayLite integrated with Outlook, I would ditch Mail again in a heartbeat.

    Its not that I don’t like Mail (its a very nice application), just that after 14 years, the Microsoft way of handling email is very intuitive and natural to me. In fact, unlike many Mac users, I am rather fond of Microsoft Office and see the 2011 version as the best yet. Yes, there are some quirks still to be worked out, but it is much more stable and quite a bit quicker than Office 2008, which I also liked and used. In fact, each version of Office for Mac OS X has improved significantly from what came before. v.X was just a port of Office 2001 to OS X, and while fully featured, crashed a lot. 2004 was stable, but slow. 2008 added the new file formats and performance improvements, particularly in its handling of Exchange accounts, though lost some features (VBA) that I didn’t use anyway.

    • Paul says:

      Yes, its seems our experiences are much different. I support Mac Office users in an office environment. I’ve been terribly disappointed in Microsoft email solutions for the past ten years. The trial of Outlook I just stopped using was slow and buggy, didn’t go a day without a crash. Entourage 2008 was faster than 2004 (but Word/Excel 2008 are terribly slow), and the EWS version of Entourage was an improvement. However the EWS version doesn’t autoconfigure well, I need to manually setup up each account, but Apple Mail autoconfigures just fine. A much touted feature of Entourage 2008 was the ability to schedule Exchange-based resources. Well, yes, you can schedule them, but if you cancel or reschedule, its hit or miss of those changes will make it to all the invitees. Many of Entourage’s problems would go away if it could operate without being in cached mode all the time. Until the cached mode is optional, Outlook will not be ready for prime-time. Server-side rule support would make it a better corporate client too.

      Compounding Outlook’s and Entourage’s problems, Word for Mac and Windows still have problems with track changes compatibility, .docx compatibility, and Word’s tendency to leave deleted data in the file, which pops up when imported into other program’s documents. You’d think for the high price we pay for Office, Microsoft could fix features in its programs, features that already work well in the free Open Office.

      • NotTellinYou says:

        @Paul, I haven’t had the issues you point to but it’s new version, there are some bugs to work out, what product doesn’t? But seriously you’re comparing “Open Office” favorably to MS Office 2011? Open Office is the definition of slooooooooow and buggy. Your statement shows a real anti-Microsoft bias. Other than price there is NO WAY Open Office compares favorably to MS Office 2011 for Mac…NO WAY.

  2. Matthew says:

    Whatever you do, do NOT try to print your address book in Outlook 2011. That is, unless you like watching the spinning beach ball every time you make the slightest change to its layout, only to have it decide not to print at all after all the waiting…

  3. Jeff says:

    I too have had a VERY different Outlook experience. In fact Gene I’ve done FAR FAR more than you and been VERY VERY successful and happy with Outlook!

    I now have imported all my emails from 1999 forward! I have hundreds of thousands, maybe millions of messages, some that have come with me all the way back to Claris Emailer! I also have three former employer databases (pst) from Outlook for Windows, as well as my last Entourage database and my latest Apple Mail. As an Office for Windows user at work I feel VERY at home with Outlook which I think is the intent.

    I hope you resolve what ever it is that’s causing you so many issues but right now, for the first time ever, I have ALL my mail in one place, and I’m VERY happy indeed!

  4. […] This post was mentioned on Twitter by Kishi Talati, Gene Steinberg. Gene Steinberg said: Here's my latest Tech Night Owl commentary: : Outlook for Mac 2011 — Still Not Ready for Prime Time http://bit.ly/hHaPPT […]

  5. msbob says:

    Eudora -> Outlook 2011 = AWFUL. 15 years of email and Contacts in Eudora imported into Outlook 2011. Only one POP account. Almost everything has been painfully bad…

    1. Outlook crashes and crashes the entire Mac
    2. Takes 30sec of pizza wheel when switching to Contacts
    -yes I do have 4000 contacts with lots of notes, but it was super snappy in Eudora
    -this makes using Contacts almost impossible
    3. Email downloads reeeaaaallllyyyy slowly in Outlook. 300 emails takes 8min, while just 1min in Eudora
    4. Sending mail…a test “hi” takes 8-12 seconds; much longer than Eduora
    -a real email with content and a small attachment takes a while
    -not a big deal, it’s in the background, but shows how slow outlook is
    5. So many holes in the UI
    6. Can’t sync with iCal calendar!?!?
    -it should not have been released without this included… it was in Entourage for cimminy sake
    7. Feels slow moving around the interface and between emails

  6. New mac user says:

    I have recently switched to a Mac and loved everything about it except Entourage. When Outlook for mac arrived on the market, I snapped it up and have been using it ever since. I HATE IT!!!!! I can’t make an entry on my calendar anymore without designating it as a meeting or an appointment. Why??? I used to put ‘to-do-‘ tasks on my Outlook calendar all the time; now when I try to simply click on a time and insert a task on the calendar, Outlook tells me to put in an email address for the other persons attending the meeting. In Windows Outlook, I could drag and drop emails into the calendar and have a ready made list for the phone call that would follow the email. In other words, when I calendared a call “Mr. Jones” the next day at 10:30 about his email, the email would be in the appointment and I could easily discuss all of the 8-9 points listed by Mr. Jones. This was tremendously useful when checking appointments on my iPhone. The calendar would show a 10:30 meeting with Mr. Jones and when I clicked on the meeting, the entire email would be displayed. This is no longer possible — I must cut and paste instead. A small inconvenience?? Maybe, but a product “improvement” that gets rid of one of the most useful features and adds time to the task as well. The loss of this single nifty feature has no good explanation. What was Microsoft thinking??? Additionally, I don’t know if I can’t figure out how to use the “Group” features or if the feature is as bad as it seems. In previous versions of Outlook, I could group contacts into various groups that made sense. For example, “friends”, “family”, “Smith Company”, “ABC Company”, etc. Click on a group, and all necessary telephone numbers were there. With Outlook for Mac this seems to be gone. I painstakingly created 15 separate categories that all appeared as “groups” in the left hand window of Outlook. Yet when I clicked on each separate group, nothing happened–no sorting by group occurs. In the right hand or middle window, where contact info occurs — name, address, phone, email, etc– nothing happens when I click on a particular group. It is as if the groups I have created have no members or entries. I can color code a contact group and enter a name for the color code, e.g., family, friends,etc., and sort by color category, but that is it. The left hand window with the groups listed remains useless. Clicking on a group does nothing. To make matters worse, Outlook the duplicates this grouping right below in a folder of files called “On My Computer”. These files are just duplicates of the groups I have created and are just as useless when clicked. Bottom Line? Instead of new features that save time, Outlook has eliminated some old features and now added time to the task.

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