Why Outlook 2011 for the Mac Remains a Nightmare

April 14th, 2011

All right, so Microsoft has finally released the Office 2011 for Mac Service Pack One. This is supposed to be a biggie, since it incorporates important security updates, along with some new features; well, make that new, plus some restored features, such as the ability to resend or redirect email in Outlook.

So far so good, but none of this amounts to anything if the app itself still isn’t working properly.

Now the regular readers in our audience know how I’ve had a love/hate relationship with Microsoft’s Mac email clients. In the days of Entourage, I struggled through damaged databases, scrambled messages locations, meaning hundreds were strewn among the wrong folders, and frequent crashes.

When Outlook 2011 arrived, I really had high hopes. After all, Microsoft claimed they had rebuilt the app in Apple’s Cocoa programming environment, the better to make it as fully compatible with Mac OS X features as possible. Yes, perhaps a feature or two didn’t make the cut, such as the redirect message feature now back in action. I was also encouraged by Microsoft’s decision not to use a monolithic database to store messages, relying on a much smaller one, and separate files for the actual messages themselves. This sensible solution also make it easier for Time Machine to perform backups.

Well, as those of you who have followed my columns know, Outlook represented one disaster after another. Maybe it was an all-new program from a programming standpoint, but that didn’t mean Microsoft didn’t migrate features, and, unfortunately, long-term bugs. I do not for a moment believe Microsoft’s Mac Business Unit rewrote Outlook from scratch. I’d think it would be closer to say they translated code from Carbon to Cocoa, and then modified and updated it in Xcode. But I’ll let the developers in our audience deal with the niceties of such a process. I’m more concerned with the results.

From the very first day, the mail folder scrambling issue persisted. It didn’t depend on whether the email was stored on my own servers or, for that matter, Apple’s MobileMe server farms. For those who explore the Linux universe, the outgoing (SMTP) servers I’ve used are Exim and QMail. The incoming mail apps are Courier and Dovecot. The rest of you will conclude that the distinctions mean nothing, and in the real world they probably don’t. They are all open source apps that follow industry-standard practices, and provide support for industry-standard email protocols.

The point is that Outlook failed then and, after installing the latest update, fails now.

Understand that I deleted the contents of the Office “Identities” folder, which is where all your messages and other data are stored. Preferences were zapped, and I recreated the accounts from scratch rather than rely on importing them from Apple Mail. I wanted as pure an environment as possible.

My email message allotment is roughly 40,000 or so, though I do make an occasional effort to nuke the older messages that I no longer need. I expect that, after accumulating this stash for over 12 years, I’m not unique. It’s highly likely that some of you store more than that, likely spread across dozens of custom folders, within several accounts on different services.

But it shouldn’t matter. Outlook is the supposed business alternative to Mail. There’s growing support for Microsoft Exchange, and it’s certainly clear that Microsoft is working  hard to clean up serious bugs. However, I do not believe that I’m the only one subjected to this folder scrambling phenomenon, nor the other areas in which Outlook delivers halting, flaky performance.

Certainly, it’s not the entire Office 2011 suite. Word seems to work quite well. Indeed it’s far snappier in most respects than any of its recent Mac predecessors. My main quibble is minor. When you open or create a new document, the window wants to pin itself on the left side of the screen, even though I continue to center them religiously. Maybe Microsoft is subtly reminding us of that highly promoted feature in Windows 7, where pinning your document windows on the sides of the screen is a feature everyone craves and continues to cherish.

To be perfectly serious about it, Microsoft is notorious for not letting the little things count. Word persisted for years with various and sundry bugs that were left unfixed. You may be surprised to realize that Word, and Excel for that matter, got their starts on the Mac. Yes, Microsoft ports lots of stuff from the Windows versions these days, but back in the 1980s, before Windows arrived, you could almost believe that Bill Gates was an ardent supporter of the Mac platform.

Now in the end, maybe my particular problems with Outlook 2011 for the Mac are unique to my system setup. But I don’t install exotic system add-ons. I buy my Macs to get work done, not to waste my waking hours filling my Mac with junk and playing around with this and that. That, to me, represents another era that’s long ago and far way.

However, I’m very stubborn, and I’ll continue to work with Outlook to see if I can find the magic configuration that addresses the most serious problems. Your advice — other than removing everything Microsoft from all my Macs of course — is welcomed.

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34 Responses to “Why Outlook 2011 for the Mac Remains a Nightmare”

  1. Manrico says:

    All PDF file attachments in Entourage emails have lost almost all bites after that all Entourage data have been imported in Outlook 2011 and are all unreadable. So when I open an email in Outlook, if email comes from Entourage, PDF attached files are 4k and all information are lost. Any solutions found?

  2. mailmergeman says:

    I run my emails via google apps and then use Microsoft Outlook as a client for only one reason. It provides a very good and simple solution to mail merge based on categories ex outlooks own “people” base.

    That works sort of ok in a windows environment but on the latest iMac it has proven to be a joke beyond believe just to be doing email. Mail merge only works by word and it cannot handle my large database. I have now installed parallels to be able to run outlook in its windows environment and it works ok. Not good but ok. I can put up with it as I only use outlook for the mail mergers and otherwise use the web-based google mail.

    Shame on you Microsoft for selling software that belongs in to the 1990ties.

  3. Jeff says:

    Since the recent update to OS X my outlook for Mac 2011 has been useless. I am on exchange. It was always a bit off in speed and functionality but now it’s unusable. Thankfully it is only on My home computer not the one in my office. It is forever looking for new mail and extremely slow to sync. My iphone and iPad are instantaneous and I cannot figure why they cannot do the same for outlook?

  4. Outlook 2011 Address Corruption | OutlookRecoveryGuide.org says:

    […] Why Outlook 2011 for the Mac Remains a Nightmare | The Tech … – Related Posts: Microsoft Outlook 2011 for the Mac — Still Not Quite… When Microsoft announced that they would build a Mac version of Outlook — their professional Windows email client — for Office 2011, I had some guarded… […]

  5. Simplified OLM to MBOX Conversion By OLM Extractor Pro | USL Software says:

    […] The manual solution to such corruption involves rebuilding the identity and many complex technical steps, which many users tend to stay away from. Here is a case of a user who faced the utter nightmare of Outlook 2011 corruption issue – https://www.technightowl.com/2011/04/why-outlook-2011-for-the-mac-remains-a-nightmare/. […]

  6. Richard says:

    I despise Outlook 2011 for Mac so much so that I’ve deleted it. It’s supposed to work with Gmail, but fat chance, it fails miserably to connect to Gmail servers, giving an error message packed with incomprehensible tech with “maybe your your id and password are wrong” which is bullsh1t. This is the 21st century yet Microsoft fails miserably to get their crap signature mail application (Outlook) to work with the world’s widest used email service (Gmail). Just how bad are these people? I for one have had enough spending hours trawling the web to find solutions to problems Microsoft should have fixed years ago.

    Any mail client is better than Outlook 2011 for Mac, even OS X’s Mail app is light years ahead of Microsoft’s pathetic half arsed excuse of an “offering”.

  7. Mun says:

    “Interesting that people are still writing about this article over four years after it was published.”

    It’s all part of the grand process of adding profitable convolusion into modern software. We had all the tools to email, browse, tinker with images and keep spreadsheets of whatever a couple of decades ago. How then were the big boys to stay in profit if they did not pioneer the trick of throwing a spanner in the works and then charging us all for taking it back out – all dressed up as an ‘upgrade’?

    Personally I always go for shareware/freeware software wherever possible. This is certainly not just about saving cash – for the most part the products are actually better as they are not mired in the duplicity that afflicts Microsoft’s products in particular. For email, Thunderbird is solid and reliable. Firefox from the same stable is a good no-nonsense browser. Open Office lacks a few features but also lacks many of the bugs in MS Office. (Even Office on Windows is a pain these days). Meanwhile, Adobe are to graphics what MS are to office ware – merchants of deception that work systematically to close down user options.

    Recently I’ve been working with the 3D animation application Blender – a truly stunning product that is utterly free of charge. I’ve realised that buying anything other than super-complex niche-market software is inherently a rip-off. It costs nothing to copy code!

    PS: steer clear of Google too… unless you want them knowing your knicker size, colour, brand and date of last washing.

  8. […] The manual solution to such corruption involves rebuilding the identity and many complex technical steps, which many users tend to stay away from. Here is a case of a user who faced the utter nightmare of Outlook 2011 corruption issue – https://www.technightowl.com/2011/04/why-outlook-2011-for-the-mac-remains-a-nightmare/. […]

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