While I live and play in the land of Apple, 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 as the Great Satan; a […]

While I live and play in the land of Apple, 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 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.

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  1. I thought this was going to be about Star Trek :(

    Seriously though, good article. An interesting read.

  2. The company I work for would most likely rather pay Microsoft $1 Billion in licensing fees that let a single Mac in the building.

  3. Vishwas Murali Tuesday, June 30, 2009

    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.

  4. 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.

    1. @James:

      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).

  5. 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

    1. 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.

  6. @Jason Burns
    Wow, great you are listening guys :)

  7. fyi, MOSS has a File Explorer view that uses WebDAV, which may behave nicer with browsers other than IE

  8. Stuart Dootson Tuesday, June 30, 2009

    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 :-(

  9. 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.

    1. I use OpenProj (an open source project management tool) and have had no problems

  10. 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. :)

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