Microsoft Outlook for Mac — Not Quite There

October 7th, 2010

I have long held a love/hate relationship with Microsoft’s Mac email software. Whereas the previous entrant, an email/contact manager known as Entourage, offered a powerful range of features, it proved endlessly flaky to me in the real world.

For one thing, those inevitable lockups and, second, the feeling I was trudging through quicksand whenever I asked the app to do some serious work. Far too often, Entourage would just bog down while retrieving email from one or more of my regular accounts, which are all IMAP by the way. I use that protocol to store the messages on the server, and thus I’m able to keep them in sync regardless of which device I use.

In any case, I looked forward to the second coming of Outlook for the Mac. Although only long-term Mac users will realize this, Microsoft had a version of Outlook available in the late 1990s, before the transition to Mac OS X.

I suppose Microsoft’s logic is that they needed a consumer-focused email client on the Mac, which is why they gave us Entourage and not Outlook.

However, Microsoft, in architecting Office 2011 for the Mac, decided we needed full, or nearly full, compatibility with the Windows version. So we have the ribbon, which is basically a context-sensitive toolbar that has drawn mixed reviews on the other platform, and Outlook, which is not offered in the basic Home and Student edition of Office 2011. I presume Microsoft expects consumers to stick with Mail or one of the other free email clients, such as Thunderbird.

While the basic email/contact manager setup in Outlook mirrors that of Entourage in large part, it’s designed as a more industrial-strength app with superior support for Exchange email servers. One key improvement, both from a performance and reliability standpoint, is keeping your messages in separate files, rather than throwing everything in one huge, monolithic database.

Outlook for the Mac has also been coded, supposedly from scratch, in Apple’s Cocoa environment, which supposedly means better compatibility with Mac OS X features, not to mention superior performance.

Now I don’t pretend to understand the underlying coding issues, but I found the overall behavior of Outlook to be extremely similar to Entourage, other than the noticeably snappier response. Sure, the dialogs are prettier, and preference settings are more Mac-like, but functionality didn’t strike me as all that different, other than the enhanced, or at least changed, feature set.

My real concern, however, is that there are some seriously annoying bugs, no doubt symptoms of the 1.0 release, which make it extremely difficult for me to use Outlook, at least for now.

There are two ways to set the app up after installation. I used both, first importing my account information, rules and signatures from Apple Mail. But after I encountered some difficulties with the setup, I went ahead and quit the program, deleted the settings files, and added the new accounts from scratch, one by one.

The import process is especially faulty. Even such granular settings as using a server’s IMAP Idle command, which lets it dispatch messages to you ahead of whatever schedule you set, wasn’t retained from Mail to Outlook. Rules were especially troublesome, and they were all non-functional without serious editing, and even then, I couldn’t achieve reliable performance.

Understand that my email rules are largely ones that dispatch a message to a specific folder if it meets certain criteria. One criterion, however, doesn’t exist in Outlook, and that’s the ability to consult message content, a feature that is supported in Mail. I had always assumed Microsoft had more powerful Rules and, except for this missing feature, maybe that’s true.

When it came to actually handling email, again I ran into some flaky behavior.

For one thing, in some accounts, I prefer to use the disclosure triangle to reveal subfolders, but I’d rather hide them in others. These simple distinctions were lost by Outlook between launches. That never happens to me in Mail.

I also ran into a problem quoting material from HTML mail in a new message window. The act of selecting and replying was sufficient for the quoted content to lose its formatting.

None of this erratic behavior was cured by cleaning out Outlook and entering my accounts from scratch. I’m also concerned that Microsoft won’t allow you to reorder accounts by drag and drop, the way you can do it in Mail. The default account, whatever it might be, is always at the top, and everything else is placed alphabetically depending on the label you attach to an account.

To add insult to injury, after I returned from a short errand, I was confronted with a prompt informing me that Microsoft had to quit the program, giving me the option to send them a report about the problem.

At this point, I’d had enough. I simply quit Outlook for good, but will be happy to revisit Microsoft’s newest Mac email/contact manager app when the inevitable maintenance update arrives. With Office 2011 for the Mac going on sale later this month, I’m sure Microsoft’s Mac Business Unit is already working on that update.

But I had hoped for something better.

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21 Responses to “Microsoft Outlook for Mac — Not Quite There”

  1. NotTellinYou says:

    I haven’t seen the sluggishness or had any crashes. I did set up from scratch though.

    This said, as a user of Outlook on Widows for work, I am VERY VERY happy to see this! It’s VERY much like the Windows version yet is still a Mac application. I think that’s a difficult balance and MS did a good job bridging the two. So kudos for that! I have no interest in running a Windows-like app on my Mac but I also don’t look forward to throwing away 10 years of application knowledge either.

    The really big benefit for home Mac users like me is the ability to import Outlook for Windows PST files. This is HUGE! It’s always been a hit or miss 3rd party utility mess to do this. Now I have 8 years worth of work related emails with all enclosures etc., nice and ready to access on my Mac. That alone sold me!

    I’m not a big MS fan but I give them a lot of credit for this release of Office. I think it’s a great release and the advent of a Cocoa version of Outlook shows that MS can write to Apple’s technologies when it makes economic sense. I hope they are able to bring the rest of the Suite up over the follow-on releases.

    • @NotTellinYou, My problem with Outlook, as I explained, was not sluggishness, but flakiness and that singular serious crash. That happened after I set up the program a second time — all from scratch.


      • NotTellinYou says:

        @Gene Steinberg,

        I understand your concern but I don’t agree with your conclusions. Using your guide I’d still be running Tiger. If I had a dollar for every 10.1, 10.2, 10.3, 10.4, 10.5, 10.6, release day crash I’d be a running on a 12-core Mac Pro.

        My issue here is you seem to completely ignore the significance of this release for those of us corporate America. Your singular nod to Exchange compatibility doesn’t do this release justice. Look, Apple Mail, is a fine basic client, and to be honest I’ll continue to use it as Outlook is more than my limited home mail needs. Even though I’m a Product Management in the Enterprise Software Group of a Fortune 5 company, I’m not able to use a Mac! It’s an unapproved platform because until now there was no Outlook peer on the Mac to manage and use corporate resources. Yes there are a few things missing but again this is 1.0.

        For many years, and not just our company, the absence of a client like this for the Mac has been the #1 roadblock to adoption. I have no great love of Microsoft but I don’t give it a personality as some do here and “hate” the company. Heck, if it was such an evil place they could have just did a minor update to Entourage and continued to stunt the growth of the Mac! But instead they went in a different direction, invested the money, and come back with a pretty good application for a version 1 product and pretty close feature parity to a version 12 product.

        Maybe I just see the glass is 1/2 full rather than 1/2 empty, regardless I hope that the release of Outlook for Mac may one day mean I can have a Mac at work.

        • @NotTellinYou, No I don’t think you quite get it. My problem with Outlook is that it’s flaky performance makes it unusable for my needs. If I required fairly extensive Exchange support, I’d put up with it. But I don’t.


          • NotTellinYou says:

            @Gene Steinberg,

            I guess that’s the key…a different frame of reference and set of needs and that’s fine!

            So to my IT brethren who are looking for a review. Let me say that I was able to connect my MacBook Pro at work to our exchange server for the first time today! I was able to book a meeting room, filled out a few forms, chatted over Communicator, and viewed my staff’s shared calendars and make changes, all for the first time. I have’t seen the “flakiness” described here but I wouldn’t take too much stock in that.

            If you have Mac users, or people that want to move to the Mac, run a pilot and check it out! I think you’ll be pleased!

  2. Andrew says:

    As an Exchange user, Outlook is a big deal for me too, and I can’t wait to buy it for my entire law office when it goes on sale.

    Entourage is okay, but its scheduling is mediocre and it does not have full support of all exchange features, including To-Do and Notes. Outlook is long overdue.

  3. Brian says:

    >Although only long-term Mac users will realize this, Microsoft had a version of Outlook available in the late >1990s, before the transition to Mac OS X.

    Yeah, it was a Classic App that people had been requesting for eons. Microsoft ONLY shipped it in an attempt to keep people from upgrading to OSX. IOW, Microsoft’s usual tactic of trying to sabotage Mac while still raking in money from it.

  4. Brian says:

    My criterion for using a MSFT app is ‘do I have any choice whatsoever’? The answer is YES, MAIL.APP. It’s working great for me. If the answer is Yes, then I won’t be ‘going Microsoft’. I’ve been burned too many time, simple as that.

    There is ONLY 1 REASON they are finally putting out OUTBREAK for Mac. MAIL.APP has just about caught up to it.
    And active sync is coming.

    So, since Apple has complete worked around their monopoly enforcing roadblock, then they might as well release this. Who knows, it could help them sell copies of this hideously overpriced SW.

    • NotTellinYou says:


      I’m really surprised by the comments here and yours where you claim that Mail has “just about caught up” to Outlook. I would say you’ve not used Outlook. I use Outlook 2007 all day at work and Mail all night at home so I think I know both pretty well and there is NO COMPARISON. Active-Sync is only a part of the story and while it will make it easier for Macs to be used with the enterprise they will not be full peers to their Windows counterparts and that’s something, like MS or not, we should all be concerned with.

      So please continue to use Mail, as I do, but don’t discount the needs of business to have more and stick to expressing your opinion for your use and not speak for those of us in IT.

  5. germ says:

    M$ chose not to support Windows Exchange server 2003, which is what my company uses, and it works with Entourage 2008. So the new Outlook is COMPLETELY USELESS to me.

    • @germ, Typical frustrating decision from Microsoft.


    • NotTellinYou says:


      According to the Ferris Study almost all organizations with up to 49 employees are on Exchange 2007. More than 60% of Exchange seats in organizations with over 10,000 employees are on Exchange 2007. About 5% of Exchange-using organizations with up to 500 employees are on Exchange 2003.

      Nothing frustrating at all! It’s simple economics, time to market constraints, code life, and corporate strategic direction with a little ROI thrown in! There are sooooooooo many reasons to get off 2003 I would fill this page with them. If your issue is cost, I would say you can’t afford MS Office anyway, so move on.

  6. Joel esler says:

    I fully agree with your experience with Outlook. I found it to be sluggish, bloated, ugly, and slow. My fans stay running the whole time I am using it. I went back to mail.

  7. Sunny Guy says:

    So many years of illegal monopoly behavior by Microsoft. They always marginalized the Mac platform, never allowing it parity with Windows for enterprise apps. If they had been broken up, perhaps the course of IT would have changed sooner. But nowadays, people are flocking to the Mac more and more.

    In any case, it is good to see that Gates is giving back the money. Even ill-gotten gains can serve a good purpose.

    Sunny Guy

  8. Don Montalvo says:

    My relationship goes back far too. Before Outlook 2011, there was Entourage, before that there was Outlook Express, before that there was Claris Emailer.
    The Claris Emailer crew left Apple to work for Microsoft. They took their excellent Claris Emailer idea and used it to create Outlook Express. Unfortunately the database, while a good idea, was volatile and prone to fail. Plus, everything (EVERYTHING) in Entourage was nestled in one monolithic database. As the database grew larger, so did the potential for implosion. Another huge flaw in the database was the archive feature (that still has me shaking my head). To archive mail, you archive to a file first, then you had to manually COMPACT the database to save space. Then, to access the archive, you had to bring it into the database all over again. Incredibly stupid, but Microsoft bought into it.

    Outlook 2011 finally (FINALLY) brings to the table well thought out and heavily tested ideas, straight from the Wintel side. With a twist, where Microsoft leverages Mac OS X core technologies. So the monolithic imploding database is gone – hello flat files! Where settings were nestled in proprietary config files, the new method leverages Apple’s incredibly well thought out and manageable “defaults” commands – hello admin ability to push out configuration settings via ssh (and thus via policy). The list goes on…

    With the good comes the bad. This is a dot-zero release. So test it on a non production Mac and learn how it works and how you can manage it. But DO NOT deploy until the big bugs (inevitable in all dot-zero releases) are patched up by Microsoft.

    My hat goes off to Microsoft. They finally (FINALLY) designed an email client with enterprise management in mind. I seriously love you Microsoft!

    (at least today)

    Don Montalvo
    Coppell, TX

    • @Don Montalvo, I used to know the original Microsoft programmers who came from Claris, and worked on Emailer.

      There are undeniable advantages in Outlook. But a lot of us, including Matt Neuburg in TidBITS, fret over the 1.0 bugs and undeveloped features.

      It’s an intriguing start, but Microsoft needs to get a maintenance update out as soon as possible to clean out the rough edges.


      • Don Montalvo says:

        Hi Gene, Yep, the sooner they release a patch the better. Unfortunately the Beta program wasn’t as open as it could have been (heck, we support 20,000+ Mac users across many companies and we couldn’t get in!). The flat file mail format is spot on, and the defaults commands are awesome. But to be honest, I didn’t spend any real time testing Outlook 2011. I figure I’ll let the others bleed…I offered Microsoft and they blew off my offer to Beta test. Anyone who remembers the Claris Emailer beta testing days know I’m quite good at putting an application through it’s paces (even Adobe would agree…hello AAMEE, APTEE and AUSST). 🙂

        Info on Adobe Application Manager Enterprise Edition (AAMEE), Adobe Update Server Setup Tool (AUSST) and Adobe Provisioning Toolkit Enterprise Edition (APTEE) can be found here:


  9. Frank W says:

    I’m a recent Mac convert, been very pleased with the experience and have been trying Outlook 2011 for these past weeks since released. The way I use email is with 8 imap accounts, all going through google apps or gmail directly and I have in store mails dating back to 1994. In Windows, I ended-up using Thunderbird and it looks like I’ll have to do the same in Mac, although Postbox has some really neat features. I don’t know how Outlook can be used reliably in a enterprise environment if it doesn’t even handle my personal and small home-based business needs. Neither the Win version 2010, nor this one can let me have a sense of confidence regarding the current updated message list. in 2011, it didn’t show me the mails of one of those 8 accounts I told you about, and when I suspected something might be wrong, opened Thunderbird and yes, there were 14 emails from the last three days, which Outlook simply didn’t do it. Apart from that, in Win or in Mac, it takes forever to update the listings of mails. So now I can’t seem to go by everyday without opening Thunderbird or Postbox just to see if there’s any expected mail response that Outlook has not updated for me. I have to quit and re-open Outlook so it will reflect the current list. This is annoying. I’ve played around with some of the accoun imap settings and hope that it will solve the issue, but frankly, I’m just about to ditch it. PS. On the first day I setup my hotmail account as well, it downloaded all messages, but had to sort the entire unified inbox with date sent, which is a bit complicated, because I get many emails from Asia (don’t know if the time difference actually affects is) and surprise surprise, two weeks later, it started downloading all hotmail messages AGAIN. There are not many setting you can experiment with. I guess the point is, I would love to use Outlook, but it can’t live up to at least my performance expectations.

  10. Willem says:

    New Mac user. Outlook Mac 2011 (30 day trial version).

    I have 5 Hotmail accounts and 2 pop accounts from my ISP. I was hoping to get a seperate environment (i.e. Inbox, Sent items etc…) for each email account, just like in Windows Live Mail. But no, I have to create rules or sort the list by account. And above that, I don’t see the subfolders I created in Hotmail (through the internet browser), nor the mails that are stored within those subfolders. Or maybe I am missing something?

    At this point I don’t see why I should switch from Apple Mail to Outlook 2011.

  11. Willem says:

    @Gene Steinberg, Thanks Gene. I see what you mean: I found a screenprint with a Gmail account in OUtlook 2011. Is that about what it looks like in your case? Here it is:

    Tried several ways to create a new Hotmail account in Outlook, but none came up in a seperate folder, let alone including subfolders. I also tried to replace the POP hotmail by IMAP, but that ended up with some sort of timeout message.

    I don’t have Gmail (and won’t have either because I don’t want to be bothered with commercial ads depending on the text I type in my emails:-)).

    Getting kind of disappointed about Outlook 2011 here….

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