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Macs in the Enterprise: A Firsthand Tale

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While I live and play in the land of Apple (s aapl), where rainbow-farting unicorns frolic in the meadows, I work in a Windows world. While being a card-carrying member of the International Brotherhood of Apple Pundits dictates otherwise, I don’t view Microsoft (s msft) as the Great Satan; a computer is but a tool to do a job. While I believe OS X is far superior to Windows, I’m not going to think a great injustice has been done if you make me use Windows.

However, a perfect storm of circumstances has required me to work remotely a greater-than-average amount of time. Since I am rarely within arm’s reach of my MacBook, my boss was gracious enough to let me use it as my primary computer. With all the discussions on what Apple has to do to get accepted in the enterprise, I found the faults actually lay more on the Microsoft side.

One disclaimer to get out of the way: As far as our IT group is concerned, my Mac is unsupported, unsanctioned, and likely an unwelcome presence. Therefore, Mac users who are actually able to call their IT groups for support may have a different experience.

File, Print and Email

One of the enterprise-related slides in Apple’s recent WWDC keynote talked up its file and print services. I can attest to this. Getting connected to our HP color printer on Windows usually involves ritual sacrifice with two goats and a chicken; on OS X it showed up as a Bonjour printer and, boom, it worked. Apple also talked up file sharing — no, not that kind of file sharing, the kind you do in an office with servers. I’ve found connecting to Windows servers can be touchy. Sometimes it works, sometimes it doesn’t, and sometimes when it doesn’t, my domain account gets locked out. Fun times.

For email, I use Microsoft Entourage to connect to our Exchange webmail server. I connect to that rather than our internal server to make it easy for me to check email when I’m not on the corporate LAN. Unfortunately, the only way I can do global address lookups is to use this AppleScript utility. Also, because of this, when I send out meeting invites, I can’t see Free/Busy information. No biggie; I can use webmail for that if I need to.

We’re also still on Exchange 2003, so none of the Exchange enhancements in Snow Leopard will help me out.

Microsoft SharePoint

I’m a tech writer for a large organization that uses Microsoft SharePoint as its document repository. Because it’s a Microsoft product, it pretty much refuses to play nice with any browser that’s not Internet Explorer. As a result, I can only perform the most basic of tasks. I can upload and approve documents, but I can’t edit a document directly on the server as I can if I’m accessing the library on Internet Explorer and a Microsoft SharePoint-compatible application. It’s kind of a pain downloading and re-uploading documents when the changes are relatively minor. Later this year, Microsoft is planning on adding the ability for Office 2008 to interact directly with SharePoint, so that might help.

I’m also responsible for some of the site administration tasks, and those only work under IE as well. If someone clicks on the “request access” link, I can give the proper access from the email I get. However, if I need to grant a user account access without that email, I need IE to perform that task — this has to do with how I choose the user in the browser; clicking the link in e-mail auto-populates some fields that don’t render properly. So far, the only way I can fully manage SharePoint is to run XP under Parallels.

Instant Messaging

We use a proprietary IM application that is PC-only. While employees can add my AIM account to their buddy lists, any group chat requests that originate on the corporate side don’t come across to Adium. Once again, the only solution is Parallels.


Like a lot of tech writers, I use Visio for my diagramming. I also like to embed the diagram as a Visio object in Word so it can be updated in-place without the source document. Simply put, there’s no way to replicate this functionality on the Mac. The closest I can come is using OmniGraffle Pro to create a Visio document. I’ve run into some serious compatibility issues on the Visio side during the conversion — curved lines and some fills get mangled.

Mac-PC Word transfers

With Word 2004, the only issues I ran into were Word documents with embedded Visio files. Now, with Word 2008, I haven’t noticed those problems. My standard template is somewhat complex and I’ve had zero issues going back and forth between the platforms.


While your experiences with Macs in the enterprise may vary, the more entrenched your organization is with Microsoft’s enterprise products, the harder your integration will be. While Microsoft is showing signs of realizing people use browsers other than Internet Explorer, making its products fully accessible by non-Microsoft operating systems is going to take a sea change within the company that could take years to even get started.

For me, the biggest issues are interacting with SharePoint and the lack of a true Visio application for OS X (and the ability to embed Visio drawings into Word 2008). While I’m looking forward to Microsoft improving SharePoint access with the current version, I’m hoping the next full release of Office has greater interactivity with Microsoft back-end products.

Right now, though, using my Mac in an enterprise environment means running Windows in a virtual machine to do some core tasks. That’s hardly an ideal situation.

45 Responses to “Macs in the Enterprise: A Firsthand Tale”

  1. It’s times like this that I thank the lord I work for a mac support company. Not only do I get to us macs exclusively in-house, but the vast majority of our clients run mac clients and servers also.

    The creative houses are used to using macs, but amazingly the general business clients we have find it totally liberating. It’s those people that are the most fun to work with; corperates without Microsoft lust as so many top dogs are blinded with.

    BTW: we use exchange (now KMS actually) and still love it.

  2. Have you tried Wine, or the commercially-supported version, CrossOver (found at They provide out-of-the-dmg support for IE and Visio, and their compatibility chart can be found here:

    Best of luck, and feel free to contact me directly.


  3. ex2bot


    Here’s my last comment about our Redmond friends.

    First, Windows ME. Ugh. Terrible OS. And for me it was ME installed on a Dell at the factory. I won’t go into all the sordid details. Check the web for customer complaints. Add in frequent system crashes (as was somewhat in the norm back then) and other baffling malfunctions, it was enough to make me want to swear off Windows.

    To be fair, XP solved the stability problem while introducing other painful issues. Such as activation. Do you know, Jason, that I can no longer activate my legal copy of XP over the Internet because I changed my virtual machine settings in VMWare one too many times. Yes, I changed the allocated memory a few times and then upgraded my notebook hard drive to 320 megs. That was enough to trigger it. Why does Microsoft make its paying customers go through telephone hell? Why? I had to type in a something like a 20 or 30 digits into the phone and then explain myself to someone halfway across the world.

    Flash forward to several months after the launch of the XBOX 360. Next gen graphics, I said. Hmm. A powerful console for the price of a high-end graphics card upgrade. The games turned out to be awesome. But I’m now playing them on my FOURTH XBOX 360. My fourth!!!! Red. Ring. of. Dammit, Microsoft!

    Jason, terrible ME, activation hell in XP, and the Red RingS of Death. We want (some of) your stuff Microsoft, but we can’t stand the abuse.

    Mac Fanbot

    P.S. Apple’s far from perfect, but they managed to pull off the unbelievable triumph of moving processor architectures (twice!). Cred. where due

  4. ex2bot

    Jason Burnes:

    I have a nit to pick with your examples contrasting Microsoft’s generous and noble legacy support with Apple’s irresponsible abandonment. You mentioned you had a dual-2 GHz Power Mac G5 that wouldn’t run Aperture due to lack of Core Image support. I also had a Power Mac G5. At worst, you would have had to do a graphics card upgrade (even the ATI 9600 would work) to run Aperture on it. Graphics card upgrades are not unheard of in the Windows world, either.


  5. Albgjr

    @Jason: This is the M$ predicament: Millions of users! M$ Management never thought through when they started taking the “whole world”… The whole world is too big for one only. Now M$ is a “follower” instead of “innovator”. 10 years in tech terms is a too long… Hardware specs changes by the minute nowadays… One cannot expect to be supported forever… You have to cut the line at one point… And that is the biggest problem that M$ has. Look at the Windows 7 requirement?!? An 1GHz 32 Bit processor?!? This is a joke. In an era of 64 bit dual core capable processors, how come you are still catering to a 1 GHz Pentium type of machine?!? You will have to draw a line here and take the hit… Or you will never be innovators anymore, just plain imitators, with lots o f Money and time to just copy what everybody else is doing better than you can do with all the resources that you have. This is the Market’s perception of M$ and where a lot of other companies are capitalizing it. Cheers…

    • so what you are basically saying is “Innovate no matter what! Screw the customer! Who cares what the real world has.”

      If we forced our customers to upgrade the way Apple does, we would probably be sitting at about the same market share and struggling with the Enterprise just like Apple.

      The reality is customers don’t upgrade that fast. 1Ghz single core processors are not only common but prevalent in the workplace, as is Office 2000, IE 6, etc.

      It’s a difference in philosophy. We believe it’s right to support our customers, not abandon them or force organizations to make what end up being multi-million dollar upgrades.

  6. I think the point that Dan is making is that there are some serious problems in designing products that can use their whole feature set only when they’re interacting with your products. No-one is slamming you personally, Andrew, nor what you’re doing. But from the outside, it’s clear that in the past, Microsoft has not cared about standards and has actively promoted lock-in via such strategies as “embrace and extend” (the Halloween memos), and questionable business tactics (Dr-DOS), as well as the whole IE-integration debacle. People still see that ugly legacy when you run into the Outlook and Sharepoint issues that the author mentions above. That’s why some of us are, unfortunately, skeptical.

  7. andrew

    I am a recent convert to MAC OS X. To get around VISIO, MINDMAP and Project tools issue, I looked at ConceptDraw Office that works well.

    As long as the .mpp or .vsd files are converted to XML format. In the mac environment just save your work in XML format and you will have seamless integration. Watchout for file size increase when you save as XML.

    I also use Office 2008 for MAC that supports exchange and i can say it works well for me coming from PC environment.

    I do agree that IT department does not want anything to do with my MAC thus support is limited.

    I also have Parallels 4 installed for those PC only applications such as financial tools that I use for approvals and Ultra Edit application.

    All in all a MAC is a good and fun product for people who want to have alternatives to PC.

    Since Microsoft has a big market share one should expect that there are a lot of applications that have been developed for PC.

    Great article

  8. Dan Farrand

    Interesting, seems like just about every problem is a manifestation of MS giving higher priority to protecting their monopoly rather than serving their customers. Mostly seems like an great argument for Open Source. Any management that allows their key infrastructure to become hostage to a single vendor and even actively defends that monopoly deserves to be laughed at.

    Our policy is to only use software that is platform agnostic. We thus eliminate an entire universe of problems while saving ourselves a lot of money.

    • Dan, sorry to take offense to your ignorant statements, and by ignorant I mean grossly uninformed. As a employee of Microsoft, I would like to set the record straight.

      I have never been in a meeting that mentioned maintaining monopolies. I design features, I create features based on direct feedback of customers. The reality is for every customer that wants updated standards support and more accessible APIs, there are a dozen existing customers with lengthy support agreements that are based on us not shifting the sands under the millions of dollars of custom development they have invested on our platforms.

      It’s not always an easy decision, but sometimes you have to weigh innovation vs. doing what’s right for your customers, all of your customers. Then there is the whole deal with not breaking IE6 to stay complieant with government contacts, EU compliancy issues, even just time, we have to make heartbreaking cuts because we just can’t get it done in time.

      Microsoft is not the big bad corporation everyone tries to make us out to be. We are a bunch of teams of passionate engineers who do our best to make our products as amazing as we can within the confines of reality. I love what I do, I love Microsoft and I am proud to be here.

    • NtroP

      @jason burns: I can sympathize with your position and predicament – to an extent. Although you and many of your coworkers may, in fact not have any problem writing interoperable code, your mention of being stuck supporting IE6 points to a large part of the problem. If you think IE6 causes you grief, imagine the *years* of pain and damage it has done to the rest of the world. Now, look me in the eye and tell me IE6 didn’t purposely break standards and isn’t the nemesis of every serious (non-MS) web developer.

      Also look me in the eye and tell me that MS’ choice of using Word’s “html” rendering in Outlook should be greeted by the rest of the world with glee. Or how your “open” xml standards can be anything but a laughingstock when the “spec” includes things like “render this blob like Word98 would” and was so obviously bribed into existence. Give me a break. I’d hope there are a few people in Redmond that have a hard time looking themselves in the mirror every morning.

      The fact that you’ve “never been in a meeting that mentioned maintaining monopolies” doesn’t surprise me. When my management knows they’re acting like asses, they don’t come right out and say it in our meetings. They just make their position clear while covering their asses like they always do.

      Microsoft may no longer be the “Big Bad Corporation” that it truly once was, but admit the fact that a vast amount of the tech world has had to suffer because of choices MS made in the past. Forgiveness might come in time, but the forgetness is harder. Especially when we see so many ghosts of MS past still haunting the world.

      I appreciate that you love your company. I’d hope you would. I also really applaud the fact that you are willing to enter into a dialogue with the rest of the world. This, more than anything, raises my view of Microsoft.

    • @NitroP: We’ll just have to agree to disagree. Microsoft is not a startup, nor are we a company like Google who can leave things in beta for years, and make no promises or commitments to any of our customers. When we sell a product, we stand by supporting our customers for 10 years on that product.

      We don’t get to make the “apple” choices like “we don’t think you need that anymore.” or “we have decided to change CPUs and will stop supporting your computer with our OS in less than 5 years.” I know those are kind of snarky comments to make, but there aren’t many companies that have the user base we do. I once bought a 12″ powerbook and a brand new 2.0 Ghz Dual Proc G5 PowerMac within a month or two each other, two months later, Aperture came out, guess what, BOTH of them were unsupported by Aperture (no core video support in the gfx) we get decimated by legal teams of we do something like that.

      I know it seems like IE6 was put out to break standards and screw everyone over, but more likely it was something like, the IE6 code base was baked before MS ever felt the HTML/CSS standards were even widely adopted enough to BE standards. (believe it or not, we like to try and create standards too) IE6 shipped in 2001, years before Firefox, years before Safari. If it shipped in 2001, most likely the code base was baked in 1999, 2000 at the latest. Microsoft is often enterprise first, and things like active-x were designed to allow customers to do things that you just couldn’t do without java in the days before ajax, dhtml, etc. were popular. But as a responsible customer, with a huge (millions) customer base using these technologies, we adjust as best and as fast as we can without pulling the rug out and screwing the customer.

      I get my guidance from my team, our customers and my brain. It has nothing to do with management not “coming out like asses” Management doesn’t design our build our software. That’s what we are for.

      I speak for everyone on our team in saying we want to make the best software we can, we want everyone to love it and we want to be a part of the community. That’s why we all blog (, we twitter (@philoking), we go to conferences, we hang out with customers, we are geeks man. We game, we goof off, we shoot each other in our offices with nerf guns. I promise you, we are just a bunch of cool dudes and dudettes that have fun doing what we do, and make the best decisions we can based on all of the environmental variables we have to consider. If that means sometimes we have to move a little slower to do right by the millions of customers that have already paid the money that put us where we are, so be it.

      btw, I am not the only MS Engineer that actively talks to the public. I do have to cya and say these are my opinions and not official MS statements, but look around, we are all over the place and love to talk to customers.

    • Mark Crump

      To back up Jason a little (fyi, I just followed you on twitter — I’m @crumpy) both Nadyne and Schweib from the MBU are heavy commenters on Macrumors and Ars respectively.

      To a certain degree, MS’s enterprise customers are PC users using IE. I worked in IT support for a long time (and still do, I’m a tech writer for an IT group), and the corportate standard is Windows/IE.

      The problem I see is, while MS is doing things soon to fix some of the issues, Mac users are dependent on IT Groups actually doing the upgrade. With budgets the way they are, that’s not always a given.

  9. Laurie D

    Very interesting article. I have a dual boot iMac at home, so can work in Mac OS X and also Win XP. I also use MS Remote Desktop to access my work PC from home; a small speed hit but very workable. Glad to see a Microsoft staffer ‘chipping in’ with 10 cents worth. Would Apple Inc. permit this type of comment? I use MS Office on both platforms and I wish there was more commonality of UI design, but I’m generally happy to use MS products. As with any software, there are always some reservations.

    • Mark Crump

      I use remote desktop connection on OS X to connect to my desktop when I’m at work for those times I need to access sharepoint real quick and don’t want to deal with Parallels.

  10. I need to access several other companies web services to access their online stuff for medical results. To do this I run Windows XP via Fusion. When I don’t mention that I am using a Mac (which they would absolutely refuse to let happen) all goes well.

    Once, I had to tell one company that I bought the PC that I needed to access their remote reports. Only then would their IT support help me configure IE to access their site. It worked, they never caught on and I continue to an iMac (running IE via Windows XP) to access their site daily.

    For 98% of my work the office uses pure native OS X 10.5, iWork, Safari and Firefox. We almost never use MS Office for internal stuff, but do need it for an occasional document written to use “proprietary” MS routines.

  11. Entourage 2008 works great with Exchange 2007…your troubles will go away when your server crew upgrades. I’m not sure, but some of the Snow Leopard stuff might also be linked to Exchange 2007, so you might not get those improvements right away.

    Sharepoint continues to be a headache…there’s nothing in that thing that requires ActiveX controls that clever folks haven’t already accomplished using standard web techniques.

    Overall, UMich has integrated things pretty well, although its still a constant uphill battle with the Windows folks even getting recognized.

    -Jeff. :)

  12. Out of 2500 workstations, I’m the only Mac at my company and receive zero support from the IT department (thank God for Google).

    I’ve had issues with my MacBook Pro bypassing network policies and inadvertently CHMODing entire directories to only be read by my machine. In lieu of MS Project I use Merlin which is a great program except that its “export to MPP or XML format” doesn’t really work (PDF is the only way I can share project plans with my team).

    On the long list of pluses, I can tether directly to my BlackBerry via Bluetooth.

  13. Stuart Dootson

    Totally agree with you re: embedding – OLE Linking and Embedding is (the?) one good thing to come from Microsoft having full control of the Windows+Office combination which (correct me if I’m wrong) OS X has never really had an equivalent of – I know there was some third part initiative (LinkBack?) to get something like that working (I believe OmniGraffle supports it!), but I’m not sure if it got too much traction :-(

  14. Without making any promises or disclosures (CYA, sorry!), we @ Microsoft are listening. Check out SharePoint 2010 when we start letting information out around October.

    Jason Burns

    • I can’t tell you how much it means to me to know that someone from MS is listening. The proof is in the pudding, so I’m withholding judgement for now, but if, in fact, MS is truly turning over a new leaf and embracing standards, it has a chance of winning me (and all those I influence) back.

  15. I have to disagree with you re: OmniGraffle. I used Visio for years, and after switching to the Mac OmniGraffle was one of the first apps I discovered. It’s so much easier to do the tasks I do (typically various types of software diagrams) that it was like a breath of fresh air.

    I didn’t worry about exporting as a Visio doc, though. For coworkers on Windows I just exported it as a PDF and that did the job just fine.

    • Mark Crump


      Oh, I LOVE OmniGraffle. However, as I mentioned our process is to embed the diagrams so they can be changed without the source document–I do a lot of network diagrams and they change over time. I can’t do that with a Graffle doc, so they have to get exported as Visios (and embedded using PC Word).

  16. Mark,
    Interesting writeup. Usually when I read about Mac and PCs, I find biased writeups. Being myself a Windows user in office and Mac in home I too have found major problems working with Visio whenever I work from home and want to get things done from Mac.