Outlook for Mac 2011 vs. Outlook for Windows 2010: Don’t Try This at Home!

Microsoft Outlook 2010

Microsoft Outlook 2010

By definition, I’m a Mac Fanboy. Just here in my home office there’s a MacPro Tower with everything on it, three MacBook Pros and two MacBooks, two Mac Minis, a dozen iPods, nanos, shuffles, several iPhones a couple of iPads, it looks like Steve Jobs threw up in here. I am a Mac lover and, what’s worse, I love Mac’s even when they don’t work the way they are supposed to.

However, I am also a DOS/Windows baby and there are certain things you just can’t do on a Mac. This has always been true. For Windows XP through Windows 7 my solution has been the Parallels desktop. It is virtual machine that allows you to run Windows or Linux programs on Intel-based Macs with excellent results.

As far as operating systems go, it’s not bad being “Bi.” I have been very happy living in a predominantly Mac world and using Parallels to access and run the only two Windows-only programs I use daily: QuickBooks Premium Accountant Edition and Visio.

Why don’t I have both Windows and Mac computers around the office? Because there was truly no need, everything was right with the world until January 2011. That’s when several very reliable sources told me that my SoHo would benefit from the features of Outlook, over the AppleMail/Daylite 3 Productivity Suite system we were using. I did some cursory research, but was told to make this switch by people who “really know” Outlook and were sure that it was the exact solution I needed.

As I said, I’m “Bi-OS” so I was happy to setup my own office in Outlook. I’ve used it on Windows computers for years and, although it is far from a perfect solution, it truly does the job.

As most of you know, Microsoft Office for Mac 2011 made its debut this year, and the big change was the addition of Outlook (which replaced the practically featureless Entourage). I was psyched. No need for Windows in the Shelly Palmer world, now Outlook is available for Mac Fanboys! After installing the program, I spent days setting up a Microsoft Exchange Server, then I designed workflow that would fit my needs. I wasn’t paying too much attention to what was missing, but I should have.

After a couple of weeks of testing Exchange and getting all of my categories and CRM stuff together, I added two additional people to the system. It was at that moment I realized that Outlook for Mac 2011 and Outlook for Windows 2010 have almost nothing to do with one another.

A few examples: Mac version does not have an email merge, cannot assign categories to contacts in the global address book, has no reliable search function and is practically useless when it comes to rules. Microsoft Office for Mac 2011 does not feature One Note, nor is it compatible with any of the Microsoft CRM products, nor does it interface with social networks, nor does it store/keep a history of your interactions with clients, and on and on and on …

What a monumental waste of time.

The fix was pretty simple, but pretty expensive. To make everything work like 92 percent of the offices in the world, I now have Parallels 6 Desktop running on all the Macs in my home office. I’ve installed purchased copies of Windows 7 on each machine. I’ve installed a licensed copy if Microsoft Office 2010 (for windows) on each machine. What will I do with the Microsoft Office for Mac 2011 installs? Well, for one thing, they will take up a lot of disk space. On the other hand, it does make opening a file a little more tricky and painful. All bad … no matter how you think about it.

Is the version of Outlook that is included with Microsoft Office for Mac 2011 a step up from AppleMail? Not really. Is it better than Gmail? No. Is it worth the time to set up Exchange for it? Absolutely not!

Which begs for the question: Why is this true? Why should Microsoft software for Mac products be so much weaker than Microsoft software products for Windows computers? The obvious answer is unsatisfactory in the extreme. If you are going to sell a crippled product to Mac owners, why bother at all?

The good news is that Parallels has a mode called “Coherence,” which allow you to open a Windows program as if it were a floating window on your Mac. It’s very slick and a very nice solution. So, expensive as it may be, our all Mac office is now running Microsoft Office 2010 for Windows everywhere and we are happy, functional, and compatible with the rest of the business world.

The bad news is that, aside from having to purchase several copies of Microsoft Office for Mac 2011 and eat them, most of the reviews I’ve seen of the product say it’s wonderful. Take if from me. Microsoft Office for Mac 2011 is in no way wonderful, nor does its version of Outlook offer any benefits at all. If you upgrade to Microsoft Office for Mac 2011 do not expect it to work like its Windows counterpart. And, like I said, don’t try this at home! Shelly Palmer




Shelly Palmer

Shelly Palmer is Managing Director, Digital Media Group at Landmark Ventures/ShellyPalmer a technology focused Investment Banking & Advisory practice specializing in M&A, Financings, Strategic Partnerships and Innovation Access. He is Fox 5 New York's On-air Tech Expert and well known for his work on Fox Television's Shelly Palmer Digital Living as well as his daily radio report on United Stations Radio Networks. For more information, visit shellypalmer.com.


  1. Viswakarma says:

    You may want to look at “ConceptDraw” as very powerful replacement for “Visio” —


  2. Brett says:

    Thanks for bringing this to our attention.

    Microsoft seems determined to extract it’s “tax” from everyone including Mac users. They deliberately cripple their Mac applications so that you ultimately have to buy Windows. You’ve been suckered. Now you’ve paid twice –something that people with Microsoft Stockholm Syndrome will grudgingly do.

    For this reason (and their past unethical business practices) I refuse to give Microsoft even one penny of my money.

    I would rather give up a bit of functionality or find workarounds than reward the evil juggernaut. If you feed it, it only grows stronger.

  3. Jerry Gepner says:

    Well said Shelly. Been down the same road…got to the same place.

  4. Tom Wyrick says:

    I think you make some very valid points here. Before I had any time to really explore Outlook 2011 for Mac myself, I recommended it to a client who was frustrated with Entourage and was considering running Outlook for Windows in a VM on his Macbook. After he bought Office 2011 and set it up, he informed me he was “still really unhappy with Outlook”. One of his key reasons was one of the same ones you point out; the inability to assign contacts to categories.

    To be fair though? I’m not sure the majority of Outlook users ever utilize the features you’re complaining about the Mac version lacking? It sounds to me like the people most unhappy with the product are the ones trying to use Outlook as a business contact manager. (That’s exactly what my client was doing.) While that’s a valid use of the product, it’s really not something the majority of Outlook users are trying to do. Many people use it in a corporate setting, where they’re simply concerned with an ability to schedule meetings and put things on their digital calendar, as well as using it as a basic email client. Weak mail-handling rules capabilities? Only a negative for “power users” — because 90% of Outlook users never use anything more than the “Out of Office” feature.

    I’m not trying to make excuses for the feature disparity between the Mac and Windows versions. I agree that this needs to be addressed. But depending on one’s needs, I can see how one review of Outlook for OS X could be glowing while another is very negative.

  5. Stephen Smith says:

    I could not agree with you more. I’m a huge fan of the Mac OS and was really excited when MSFT released the 2011 version of office. Not only does Outlook suffer from the issues mentioned above – it also has significant issues when connecting to Microsoft’s hosted exchange service (loses connectivity all of the time, has “http” errors that force emails to go into the draft box instead of sending)… The excel product also has real performance issues when dealing with very large spreadsheets — the windows version zips through them (even under parallels) and the mac version just limps along at best.

    I had such high hopes for the product… and just as you are – I’m forced to run parallels to get the functionality I need.

  6. John says:

    Found a site that says Outlook for Mac DOES DO email merge.

    Important for me, as I am contemplating a move to Mac.

    Here’s the site: http://www.macworld.com/article/158391/2011/03/mail_merge_word.html

  7. Jean-Martin says:

    Congrats Shelly for such a great article!!
    It did shed the light I needed to decide if I was going to jump on the Outlook 2011 for Mac.
    Now I know I will stick with my Parrallels 6/Outlook 2010 for Windows XP setup.

    I have had a Macbook Pro since 2008 and I love it. However I am still trying to find out how to move away 100% from windows. I have been using Outlook for Windows for years. Hence that is “almost” the only reason why I still need Windows around. I cant wait for a Mac App that can replace my Outlook.

    Now I would be very interested in finding out how you deal with your iphone/contacts synchornisation.
    I have just purchased my 1st iPhone4 replacing my former Blackberry.
    Since my purchase I have been struggling “A LOT” to find a reliable “syncer” evaluating different solutions.
    I have tried several paths with no success including :
    1- iTunes/iPhone for Windows sync with Outlook 2010 on Windows XP Under parallels 6
    sometimes it just crashes, other time the contacts has no data except for first and last name
    2-mobileme for windows
    After some incoherent syncs between Outlook and Mobileme I decide to perform some tests.
    I uploaded successfully to MobileMe some trial contacts from my Macbook Address book.
    Then I started from an empty contact folder in Outllook to see if I could down all my contacts in Mobileme to Outlook.
    Not all contacts where downloaded and many contacts had blanks fields.

    I am running out of ideas as to how to keep my iPhone up to date with my Outlook contacts.
    Any advice would be appreciated.


  8. BK says:

    This is a great article. I think it illuminates a larger point – Macs are simply not as capable for highly productive users that must juggle professional calendars, email, contacts, and to-do lists. It’s not essential that I have Outlook to do this, but I need something to do it. I guess I sort of assumed that handling this stuff would be table stakes for Mac, and that I could find a way to do the basic things I took for granted in Windows. Not so. My realization is that Apple fantards simply leave different lives than me – lives that don’t require the same kinds of communication and coordination that 90%+ professionals in the business world must have.

    I am six months into my own transition from Windows7 to Mac, and the shortcomings of Outlook on Mac are at the top of my list of grievances, and will ultimately be at the top of my list of reasons for retreating back to Windows (anybody want to buy a used iMac and Macbook?).

  9. Peter says:

    After hours and hours moving from my windows outlook to mac 2011 outlook I have to concur with the review. Outlook for Mac just does not work. Rules are intermittent and unpredictable – such a crucial mail feature rendered useless. My contacts came in with the PST file import, Then disappeared without a trace. Absolutely do not waste your time on Outlook for Mac 2011

  10. Pinoroho says:

    Thank you Shelly for the great insight.  I have been a longtime Windows user and have been making the switch, albeit slowly but surely to Apple.  And finding all kinds of pitfalls and frustration along the way. It all started innocuously with a little handheld iPhone, then iPad, and now I have just purchased my first Macbook Pro and iMac.  One of my goals was to utilize iCal with my iPhone for Reminders between the iPhone and iMac. But there seems to be a “bug?” in Lion that keeps you from editing a Reminder on the iMac if it is setup and typed into the iPhone telling the Reminder to repeat.  It will sync to iCal, but you cannot edit it, because iCal Reminders do not have an option to repeat.  More frustration. So, as much of a “bad taste” Microsoft has left in my mouth over the years, I have opted for the “bi-OS” option.  I have been looking into getting MS Office, because my shiny new Mac isn’t doing exactly what I would like it to.  So I searched the question: ” Install Office 2011 on an iMac or Windows 7 with Parallels.” and you came up in Google to save me literally a weeks worth of setup time and pending frustration.  Thank you.  You are now in my bookmarks bar……in Safari of course.

  11. Dhom88 says:

    Shelly, thanks for posting your experience with Office:mac.  I just switched from Windows to Mac OS. So far, running Windows Office 2010 in VMWare Fusion (in Unity mode) is 99% seamless.  I’m still paying with keyboard shortcut mappings to make my user experience consistent, but it sounds like I made the right choice to stick with Windows Office in a VM rather than try to use Office:mac.

  12. Leyzer1950 says:

    I am interested in Shelley’s observation that Outlook for Mac “is practically useless when it comes to rules.” I just got a Macbook Air with Outlook, and the menus that are supposed to set up rules (in Tools, the Home toolbar, and the context menu) have only “edit rule” and “apply.” There is no option for creating rules. Has anyone seen this, or any idea what could cause it?

  13. Ronniead says:

    I just installed Outlook 2011….imported my pst file…but terribly dissapointed. All my rules, and email accounts didnt get imported. I have over 30 rules, and around 20 accounts. It will be faster for me to just set up outlook in paralells and copy the pst file over directly. I wish I didn’t have to, but this is just way to frustrating.

  14. Sa668 says:

    My biggest problem in Outlook for Mac 2011 is Calendar Event Reminder NOT displaying.  I hear a sound but there is nothing visual – no pop-up window nothing.  I hear a sound and I have to hunt through outlook to find out what the sound was related to.

    Is anyone else experiencing this problem?  In Outlook for Windows when a calendar event, meeting or appointment is due I get a visual alert – a box pops-up on my desktop ontop of everything telling me I have something to do. 

    I find myself missing meetings and appointments because of this. 

  15. Punter says:

    I couldn’t agree more with your review and assessment. I’m coming from the Windows world – and my business had Office as its main productivity tool, not the least being Outlook-Exchange. In fact Office 2011 for the Mac was the reason I agreed to move into a mixed Mac/Win environment in our office. And just like you, I was disappointed with Outlook for the Mac. It’s as if the Mac development team tried to copy the functionality using faded fax copies of the original Windows based product.  Although it does have some interesting features that its distant Windows relative does not posess, it fails miserably when it comes to business grade functionality. I’m also installing Parallels – for the sole reasons of running Outlook for Windows.  

  16. Ginad says:

    I am wondering if there is a way to have the Business Contact Manager with a Mac and a PC. I am on a Mac and my boss is on a PC? We need to have this function? If you do Parallels, (which I have tried) then don’t you need to have an anti-virus on you mac? That defeats the purpose of the Mac. 

  17. Jaroko says:

    a forever power user of Outlook/Exhcange and about as far from a Mac fanboy as
    there is. That said, my laptop of choice currently is my Macbook Air. I am a
    huge fan of Apple’s industrial design and hardware engineering (minus, of
    course, their constant choice to forego accepted standards in favor of their
    own proprietary connections: i.e. displayport instead of HDMI, Ipod/Iphone dock
    connector instead of mini/micro USB…but I digress.). When I got my shiny new
    Mac after about 2 years operating completely sans Mac, I was pretty excited. I
    relearned Mac OS with joy, played with all the new features, and was having a
    lot of fun. Then reality set in when I had to do some actual work. The email
    system of the Mac seemed OK at first as I set it up to deal with my 4 separate
    email accounts: 1 Gmail, 1 Hotmail, and 2 exchange. I loved that I could look
    at one inbox (just like on my IPhone) and see everything but still keep
    everything in their own separate accounts. That’s where the positives of Mac
    mail/calendar/contact system ends for me however. I was just too used to the
    functionality in Outlook, especially for Exchange connections, to work
    efficiently on Mac Mail. I’m also a Microsoft Partner and Action Pack and
    Tech-Net subscriber so I downloaded Office 2011 for Mac and thought my problems
    would be solved. Unfortunately that is not the case. Although I think that
    Outlook 2011 for Mac is a far cry better than Mac Mail, it pales in comparison
    to the functionality of Outlook on the PC. I have found it to be
    very much in keeping, however, with the general Mac mentality that simpler is
    better. To me it seems nearly all Mac software, especially that designed by
    Apple, lacks user control inherent in the PC counterparts, including the
    operating system itself. The whole “it just works” thing has become
    the driving force in development. For those of us who don’t really want it to
    “just work” but work the way we want it to, and are technical people,
    it can be a little frustrating to say the least. I’m not writing them off for
    my own use completely, but I still prefer a 2 or three screen monster PC to get real work
    done, and real management of my business. As for surfing the web, scanning my
    email, goofing around with video and pictures, even my relatively powerless Mac
    Air shows me that those things are in the Mac wheelhouse. I’m sure I would love
    to have a beautiful 27 inch iMac sitting on my desk connected elegantly to a 2nd
    perfect 27 inch Mac display through a single displayport cord, but for 1/3 the
    price, for now I’ll give up that beautiful appearance and excellent
    mouse/trackpad interface for actually being able to get work done the way I
    want. I hope that as Mac continues to expand its customer base and business penetration, they add back some of the user control for the power user.  For the people I support however, I’m pushing Mac Mac Mac, (and I would recommend Office 2011) for most of
    them, although, the simplicity may ultimately obsolesce my importance.

  18. Pita says:

    couldn’t agree more. Outlook for MAC is a huge disappointment. I considered parallels but on my MacAir it would be too heavy to install Win7 and Outlook since HD is just 128mb. Incredible how many people consider this option. To me, it’s too obvious what MSFT is doing here. It’s a shame.

  19. jorge says:

    Hi All, I am a mac fanboy, I have used macs for more than 15 years, and I have outlook installed and working perfectly; emails, calendars, alarms, notifications, including rules. I am graphic/web specialist, so in my field is all about visual communication, when I design an email template to be used in Bronto or GovDelivery interface, guess what? all the styling (including some CSS3 code) it shows up in outlook/ mac, but no in pc (I have to test all the template in all the email clients to see if they will look just right ). So I think it is more a setting issue than anything else. How to fix those issues? I have no idea, because the IT guys take care of that. Mac always was more compatible with pc, than pc with mac. Both system are 90% different, the most common thing between both of them is the core processor, so before to get in the mac world, you may have to analyze your needs and forget about the “style and sexy looking of apple products”, it is more based on the design and visual communication world than any other business, and be a mac fanboy with a strong knowledge of what apple’s world is about. For sure it is not a pc.

  20. Ana says:

    Avoid using Microsoft products on Mac and you’ll see how beautiful is the world!

  21. ottoman says:

    impressively well summarised, Thank you! Every problem and more I have discovered is covered here, best post i’ve seen and I’ve spent hours, looking for answers to my troubles with Outlook 2011. Microslop software! Rule number one with Microsoft – NEVER buy the first release!
    Beta beta beta

  22. Chip Rodgers says:

    Totally agree Shelly. I have been using Outlook on PCs for many years and just moved to a Mac. I’m having trouble adjusting to the MANY deficiencies in the Mac version. For example:

    – No paste options. When I paste a spreadsheet into an email, it only allows me to put the full editable spreadsheet text in there. With PC Outlook, there are 4-5 different options of how to paste something into the email (spreadsheet, text, image, etc)

    – When pasting a screenshot into an email, there is no editability on the image. Can’t grab corners and resize, can’t adjust in any way. With PC version, you can do all functions that you can do in PPT for example, resize, border, shadow, compress, etc, etc.

    – In PC version of Outlook, meeting invitations have full editing capabilities. So you can use bullet pointing, text format, etc. Mac version has no formatting ability like that in your calendar entries or meeting requests.

    – If you want a formatted signature, it will be inserted on both new emails as well as replies, forwards, etc. I prefer to only have my formatted signature on new emails. Replies with no signature. With Mac version, it’s all or nothing. So I’ve chosen to turn it off so I need to remember to insert manually on new emails.

    – Contacts is horrible. There is no formatting like the contact card format. Only one format — a list of names with preview on the right.
    – Can’t customize the ribbon bar. What?? I’d like to move the delete key over to the right where it’s closer to my email list. Can’t do it.
    – Can’t put any favorites at the top of your list of folders. Can’t hold the few most used areas like your inbox at the top. When you scroll down to drag things into folders, you have to scroll back up to the top to get back to the inbox.
    – Contact search appears to not be working at all. Search for any part of a person’s name and it comes back with no search results. Very frustrating.

    This is all very frustrating. Sounds like I will have to buy Parallels and set up a windows version. More work and aggravation.

  23. Jess says:

    Do you know of any CRM that works with Outlook for MAC or a contact management tool for MAC that synchronizes with Outlook for MAC? :-(


  24. Jim Scarff says:

    Export Outlook files from Mac to Windows. When I temporarily tried a Mac in the spring of 2011, I imported my outlook.pst file from Windows into Outlook for Mail. However, a couple of months later when I needed to when I needed to switch back to Windows, my data in Outlook for Windows was stranded, there being no easy way to export it in a format that could be read by Outlook for Windows. This also made it extremely difficult to synchronize my Outlook file on my Windows desktop with the Outlook file on the Mac.

    The only way I could get the data on Outlook for Mac back to the Windows version was to upload it to an IMAP account then download it, or hire an outside firm to do the conversion for me at over $150 each time. And this did not bring over the contacts or calendar.

    In Outlook for Windows it was easy to edit the subject line of received e-mails to make it easier to find them later (e.g. “New publications this week…” to “Killer whale physiology”). In Outlook for Windows it was only possible to change the subject line with the addition of some 3rd party software add-on.

  25. Mike says:

    I had nearly the identical experience and settled on the same solution. Perhaps the theme here is that the utter uselessness of Outlook 2011 drives sales of Windows OS and Office 2010/2013.

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