Why Outlook 2011 for the Mac Remains a Nightmare
April 14th, 2011All 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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Anyone using Microsoft applications on a Mac in 2011 get all the pain and frustration they deserve.
Time to put them all to the sword.
Outlook is garbage, just like Entourage is garbage. Lots of features, but a basic, really vulnerable structural problem shows that the MS engineers have no learning curve,.
It keeps its info in a single database, which, if damaged, is irrecoverable. I simply don’t have that kind of faith in MS.
We are waiting for Kerio Connect to support Active Synch in Outlook 2011 before I deploy it. Your issues don’t give me much confidence though.
I had minor issues when I initially deployed Outlook 2011, and one support call to Microsoft (had me create a new profile rather than import my Entourage profile) fixed everything. There were missing features, such as sync and resend, the former is sort of fixed (Apple is moving on from sync services) and the latter back in action with SP1.
I use Outlook for my personal and military email accounts (Exchange and IMAP) and Apple Mail for my business accounts (Exchange and POP3). Backwards yes, but its more on account of DayLite’s Mail integration than any shortcoming in Outlook, which I am very pleased with thus far.
Honestly, I see Office 2011 much the way I saw Office 1998; a return of the Mac BU to creating solid Mac software.
Have read what you say but don’t understand. I used Entourage and imported my mail from that into Outlook 2011. It all works fine. The window doesn’t open to the side of the screen and since SP1, Outlook launches much faster and yes, it is good to get back the odd missing feature. What really bugs me though, is that if the Mac BU developed Outlook in the Cocoa environment, why am I still having to use cmd + to zoom when I should just need to use finger swipes/ movements on the trackpad? They didn’t fix that!
People moaned about Entourage and Outlook Express before that. But really, they do the job. I just want to create, send and receive emails then file those I want to keep and delete the rest. Outlook does that fine however, I don’t tend to let my database grow too big, certainly not into the tens of thousands. I seem to recall that somewhere there is advice that 7000 mail messages is the maximum you should keep live.
Just because they’ve finally brought Outlook back to OS X doesn’t mean they’re going to make it work well with third-party email servers. Their goal is to get you spending the serious money on an Exchange server where they can rip you off on client licenses. It took them until Outlook 2010 to finally have deleted IMAP messages move to the server’s trash folder.
I’m mad as hell and I’m not going to take it anymore!
Microsoft is digging! R.I.P
Reported the lack of mail merge excel>word>outlook in October, and every month after. A fix in SP1? No…
Honestly I cannot support your feelings about Outlook. It might be that I am working in a billion dollar company with offices all over the world. Maybe Exchange Server is the newest and best administered version. But honestly the arrival of Outlook 2011 was the biggest relief ever. And it was made available companywide just weeks after the final shipping. So there must be reasons. Maybe it is in connection with Exchange only and I do not oversee the problems people have with other backends. For us there is only Live Meeting for Mac what is heavily missing…
Marcus
As for me, I’d be happy to work with Outlook 2011, except for my particular issues, which had nothing to do with Exchange. I was just connecting to MobileMe and a very standard Web server with a pretty general email setup — other than enhanced spam filtering, of course.
Peace,
Gene
I use Apple Mail at work.
My IMAP account at work currently contains 27343 messages in 17 folders and takes up 1.7GB on our Snow Leopard server. I have a further 8576 old messages stored locally in 13 folders.
Mail is also configured for my MobileMe account with 3192 messages occupying 236MB on the server.
I used to use Entourage at home, but after dealing with too many corrupt databases (both mine and those of people I provided support for) I switched to Apple Mail.
The last time I dealt with Exchange was back in 2002 and all employees had desktop PCs with Outlook for Windows.
Thank you for this post. I had a near emotional breakdown after realizing the database was going to corrupt as often with Outlook 2011 as it did with Entourage. I held my breath, and held on to what proved to be false hope, waiting for Outlook to replace Entourage.
Our Enterprise is on Exchange (which I really like) and due to the way we use group account to share central resource calendars iCal isn’t an option. I personally stayed on Mail.app/iCal.app and just open Outlook when I have to. I’ve migrated my local folders containing more than 40K of messages from computer to computer to computer over the last 6 plus years in Mail. Never a single corruption, never a single problem.
I care very little about features. I support around 30 users and I get at least one database corruption a day. Some rebuild, some don’t. It’s a huge amount of wasted time and money. I absolutely can’t trust any data in local folders in Outlook. The database will corrupt and take you out just when you really need to be in your client.
I hope that Microsoft is doing this to make the mac platform seem as though it’s not enterprise ready. I’ve never used an email client that can’t reliably store emails in folders. I can only hope this is intentional?
I’m very very disappointed in SP1. Yes, they fixed the calendar sync issue with iCal (whoopee), but as for the rest, Outlook 2011 is as rubbish as ever. It has major performance issues and somewhere in there, there’s a HUGE bug…
My employer uses an Exchange server. Yesterday, after installing the SP1 update, I naïvely thought this would be a good time to do some email cleaning : filing and trashing old mails. Big mistake!
I only have 2500 mails, but after about ten minutes of moving groups mails to folders, trashing some, etc, the whole Mac suddenly slowed to a crawl. Outlook was apparently syncing my changes to the Exchange server “live” and for some reason, it got its wires crossed in a big, bad way. It brought my whole Mac to its knees, slowing it down to the point where it was impossible to continue working.
Worse, not even a Force-Quit would help. I had no choice but to hit the Power button and turn it off. This happened no less than ten times yesterday! Every time I restarted the Mac and launched Outlook, after a couple of minutes it just took up where it left off, swamping everything in molasses.
I suspect a major memory leak, because even on the rare occasions where I was able to quit open apps, or where nothing else was running, the Mac remained crippled – even with only Finder open. Force-Quit/Relaunch was useless.
It was the worst day’s computing I’ve had in many years. Roll on Lion and the updated Apple Mail. If it plays well with Exchange I won’t hesitate for more than one second!
Why not use VMWare and run Outlook in its (now) native environment ?
I’m not sure what the benefit of only going half way M$ could be.
That way, you’ll get the bloated, ill designed, Microsoft software minus the Mac porting bugs from second hand, ugly step child, development team.
Just allowed the update today. Unfortunately, it did not instruct me to restart before using. Just said that update was completed.
Started up Outlook; It attempted to rebuild the db, which it said it could not do because the db was from an older version of outlook. Said I should rebuild with the older version. Which of course is not there. After our IT dept. futzed for 2 hours, we gave up. Of course I have my exchange mail, but local folders are gone.
Apparently, the update should have made me restart 1rst. 8-(.
Am trying to just the local folders from a backup but am not having success.
Assuming your email is IMAP, you should be able to just start from scratch, and reenter all your accounts and have it retrieve your messages from the Exchange Server.
Also, is there something with your Exchange setup where you can’t just use Apple Mail?
Peace,
Gene
I just migrated to a MAC and pulled down Outlook 2011 as the last 15 years of my emails are spread across various PSTs from different companies / projects. Seems like Outlook would be the easiest way to go … I can’t f!@#ing believe that there is an unresolved bug that won’t allow you to change any folder names in IMAP or POP accounts … I mean … really? This is the culmination of how many man hours to produce what would otherwise be a reasonably useful product, and because of this one bug, it has devolved into a monumental waste of time.
It really is beyond words that I have to look for a work around via various scripts, or a $12.95 fix to convert my PST to MBX (O2M from Little Machines) because Outlook 2011 for MAC sucks as bad as it does … What a let down. If anyone knows of a fix … I would be interested to hear it. I’ve heard of the “Go Offline” workaround to create or rename local IMAP folders … which doesn’t work. It folder name dialog box still closes about a half second after I select “rename” … I might get a couple of keystrokes in … It took me 5 tries to get a folder renamed from “Unnamed Folder” to “Family”. Worthless.
I see that the supporter of Office on the Mac (Marcus) writes ‘the arrival of Outlook 2011 was the biggest relief ever.’ Is this all that decades of IT development can amount to? ‘Relief’ is something that you get when you deposit unwanted body substances in the bathroom!
I’m looking at this post because after a couple of years of semi-frustrating use of this bloatware (Office on Mac AND Windows) I now find that the Outlook ‘Find’ tools are totally non-functional on my Mac install. I didn’t do anything – it just suddenly decided not to find any mail, contacts or whatever – no matter how basic or comprehensive the search is. It sees my contacts when I start to type their names into an address field but it now NEVER FINDS ANYTHING AT ALL in the Find/Search tools. Like many, I’ve a shed load of emails that I often want to refer to by a search… now I am stuffed. Thanks Microsoft… I genuinely found Office 97 more reliable and intuitive and it was free of all the pointless add-ons that have since been introduced to enforce MS’s monopolistic market position.
On a closing note… I might be going mad but it increasingly seems to me that IT represents the ultimate failure of a market-based social structure. Far from realising the huge new benefits that should be available from the ease with which digital info and code can be copied and replicated ad infinitum, what we have with Microsoft, Apple, Google & Co is a situation in which everything is done purely to exploit people’s dependency on whatever system they are hooked on. By moving the technical goalposts, the products of yesteryear that could remain perfectly viable are actually consigned to the bin – not for any user benefits, but purely so that the user is coerced into spending more money for something more convoluted and susceptible to vulnerabilities. Is it any surprise that Microsoft are also hugely active in security products? The situation is like a bank that takes your investments, steals them, and then adds charges you to deal with the lack of security that they sold you.
Don’t you love humans?
Can anyone help me get out of outlook for Mac and back to outlook on PC please? i am literally a hostage!!!!
can anyone explain why Microsoft would not have a simple program where i can easily migrate my emails back to a PC?
@Yosi, This may be an elementary issue, but if your accounts are IMAP, and you’ve properly mapped local folders to the server folders, you don’t need a special migration program. Just set up the accounts on your new computer, and the messages will be properly retrieved in due course.
As for me, I don’t like Outlook for Mac or Windows, and if I were forced to use Windows 8 for any amount of time, I’d be very concerned over what to choose for email. The standard W8 email app is pathetic.
Peace,
Gene
Yep, a real frustrating package for anyone coming out of a Outlook 2010 or even an Outlook 2007 environment. It’s cost me so much time and driven me so crazy that I ended up also starting a blog about it as a warning to others called Apple Captive.
http://applecaptive.blogspot.com
I hope the people at Microsoft are having a good laugh.
@Apple Captive, Unless you must have compatibility with an Exchange Server in a way that is not supported in Apple Mail, nobody forces you to use Outlook 2011. I still find it essentially unusable. In other words, your complaint is, frankly, not valid for most people considering a Mac.
Peace,
Gene
” … nobody forces you to use Outlook 2011 … ”
This is entirely true but also true of ANY software.
Being involved in graphics and music I bought a Mac really to be less out of the flow as regards what these industries prefer. I was exclusively on Windows until then but would now say that for dedicated purposes the Mac just feels more stable than Windows which is a real Jack-of-all-trades-Master-of-none solution.
Unfortunately I do need that compatibility with Microsoft Exchange so am still battling with Office for Mac 2011.
We’ve also had to buy one employee on Windows a standalone copy of Outlook which cost a lot of money and is hated by the user.
I find Microsoft’s strategy really foul. They only seem to support Office on the Mac to the extent that they want more revenue whilst at the same time being able to say ‘Well that problem doesn’t exist in the Windows environment’. I’m still heavily buried in Windows but would, given the opportunity, now always opt for Mac (if price was no object) or Linux is budget was important.
Sadly, I have no tech answers for anyone looking for them and expect that this mess will continue to evolve rather than improve, thanks to Microsoft’s abusive market position and lack of morality.
2011 for MAC – encountered sooo many problems its ridiculous, MS email software is as close as we get to anything else PC based and im glad thats it. Search bOx deoesnt work, auto detect email doesnt work, cant customise the buttons to remove the ones we dont use, about 70% of them. unstable and crashes trying to use a signature. 2011 for MAC your very very bad… MS your gone.
@pissedorf, As updates appear, I return to it to see if I can make it work. Or convince myself to like it. I fail on both counts.
Peace,
Gene
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?
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.
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?
[…] 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… […]
[…] 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 – http://www.technightowl.com/2011/04/why-outlook-2011-for-the-mac-remains-a-nightmare/. […]
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”.
@Richard, Interesting that people are still writing about this article over four years after it was published.
Peace,
Gene
“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.
[…] 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 – http://www.technightowl.com/2011/04/why-outlook-2011-for-the-mac-remains-a-nightmare/. […]