Apple OSX Lion & Microsoft Exchange: The End of Fanboy Days

mac-outlook

Outlook 2011

Back in April 2011 I wrote a scathing review of Microsoft Office 2011 for Mac.  I was specifically distressed by the highly touted addition of Microsoft Outlook, because after careful testing, I could reach only one conclusion: it sucks.  My solution for the total suckage of Outlook for Mac 2011 was to run Microsoft Office for Windows 2010 on the Macs around my office using a program called Parallels that (in simple terms) allows you to run Windows and Windows compatible programs on your Mac.

This sub-optimal solution became even more sub-optimal as we added more people to Microsoft Exchange.  So, some intrepid souls decided to try something radical … they used Apple Mail, iCal and Address Book to interface with Microsoft Exchange.  Low and behold … praise be to Jobs … it worked.  There were happy Mac Fanboys all over the office singing the praises of Cupertino and loving the fact that Apple was in the business of doing business.

Hallelujah, Apple got its enterprise on.  Time for Snow Leopard sock puppets! We were all thinking about making the switch.  But … just as quickly as we had fallen in love with the Apple Mail/Microsoft Exchange solution, came the End of Fanboy Days … OSX Lion 10.7.x.

There are many wonderful things I can say about Apple’s OSX Lion operating system, but compatibility with Microsoft Exchange isn’t on the list.

All of our new MacBook Air computers came with OSX Lion 10.7.x preinstalled.  As I am fond of saying, my MacBook Air is simply the finest computer I have ever owned … except for one small issue … iCal under Lion is incompatible with Microsoft Exchange.  A few minutes Googling the error message confirmed our worst fears – Apple knows about the bug and has done nothing to fix it.

The issue is subtle, but it is a deal breaker.  Under certain conditions, you can’t send and receive meeting requests and get the title of the meeting to show up in iCal.  You get a blank meeting.  When it happens the first time, you assume that you have done something wrong.  After a few more times, you ask your system admin what’s up.  By the 10th time you lose your meeting info, you type the issue into Google … that’s when the enormity of the situation hits you.  You’ve just opted into a workflow that is completely useless for the doing of business with 92% of the business world.  Want a list of compatibly issues; just search for your favorite flavor – it’s not pretty.

To say that we did everything to solve this would be to understate the issue.  No eclectic techno-geeky trick was left untried.  Bribes to friends at Apple, calls out to hackers, even a FB plea to Fanboys around the world … all to no avail. :(

The ultimate solution is so sad, I have named it the End of Fanboy Days.  We are now the proud owners of a bunch of 17″ HP ProBook 4730s running Microsoft Office Professional over Windows 7 Professional.  HP’s Value Added Reseller (VAR) channel rocks!  If you ever need a bunch of computers that are sturdy, built for business, free of bloatware and ready to use when you get them, call your favorite HP VAR.  Talk about flawless integration with Microsoft Exchange — everything works so perfectly, it’s sinful!

I still carry my MacBook Air.  For me, it is still the ultimate computer in the galaxy.  I don’t mind having the crippled Microsoft Office for Mac 2011 running on this computer because I don’t do any administrative functions with it.  But, if I didn’t have an executive admin and an administrative assistant who keep my calendar, I would have to choose between crippled Outlook functions or non-functional appointment compatibility in iCal.  Two unacceptable options.

If you don’t use your computer for business and don’t have to have a computer that is 100% Microsoft Exchange compatible, nothing here really concerns you.  However, if you are truly trying to use a Mac running OSX Lion 10.7.x as a business tool to interoperate in Microsoft Exchange environment … sadly, it is truly the End of Fanboy Days.

Author:

Shelly Palmer

Shelly Palmer is Fox 5 New York's On-air Tech Expert (WNYW-TV) and the host of Fox Television's monthly show Shelly Palmer Digital Living. He also hosts United Stations Radio Network's, Shelly Palmer Digital Living Daily, a daily syndicated radio report that features insightful commentary and a unique insiders take on the biggest stories in technology, media, and entertainment. He is Managing Director of Advanced Media Ventures Group, LLC an industry-leading advisory and business development firm and a member of the Executive Committee of the National Academy of Television Arts & Sciences (the organization that bestows the coveted Emmy® Awards).

  • http://www.jondale.com Jon Dale

    Shelly,

    A true fanboy would have just switched from Exchange to Google Apps. All of the core functionality, a fraction of the cost and completely completely compatible with all the Mac and iOS apps.

    Every organization (Mac and PC based, large and small) that I’ve seen make this transition has loved it and would never go back.

    • KW

      Actually Google cal and iCal have a problem. I have many recurring events. Try deleting one instance in iCal. 70% of the time, google refuses to delete it or gives an error. I am now just using iCloud. 

  • http://www.facebook.com/jamescjoyce James Joyce

    I agree with Jon.  Google Apps is clean, great (and cheap) and sharing files and runs well with iCal, Apple Mail and Address Book.  When I switched to Mac 3-4 years ago, I just stopped using Outlook cause it was just clunky on a Mac.  It was painful at first as all new things are (like Facebook Timeline), but once you make the switch and realize that there is another way and it’s no worse, then you wonder what all the fuss was about.

  • Shelly Palmer

    You guys are right, Google is an option.  But, we own our Exchange server and it’s in our racks.  Handing off that much proprietary IP to Google and hoping they do a good job maintaining it for us forever is not interesting to me at all.

  • Neil Chapman

    Come on, Shelly!  Get yer Goog on.  I’ve struggled with this in my law office also.  But I’ve “outsourced” my IT with Dropbox, Evernote and Google Apps.  I’m afraid that you are on the wrong side of history . . . :)

    • Shelly Palmer

      Neil — Thanks for the post. I have my Goog on. I love Google Apps, am addicted to Dropbox and Evernote and use them extensively. That said, Dropbox is a copy of a directory on a storage device that is in my possession.  Evernote is also an “add-on” utility.  Google Apps are awesome, but they do not force me to store my docs or spreadsheets exclusively in the cloud.  So, your examples are related to, but not really applicable to the thesis or issues I am concerned with.

      On the other hand, Gmail correspondence is not in my possession unless I copy 100% of it to a storage device I own.  

      It’s great to offload systems that are not your core business (and even some that are.) We use Salesforce, for example, but it is backed-up locally.  

      As of this writing, as important as txt, Twitter and FB messaging are, email is the core communicative application for my business, and it is where (sadly) the greatest amount of institutional memory lives.  

      Email/Contacts/Calendar must be flawless, trusted, safe and redundantly backed-up — it is a non-negotiable fact of my digital life.  Exchange sucks.  In fact, it sucks huge … but it provides flawless email/contacts/calendar, it is trusted, safe and we can redundantly back it up.  Unfortunately, to take full advantage of Exchange, I have to diminish my Fanboy status to kind-of-Fanboy.  ;)

  • Mario Faria

    I am a heavy Microsoft Outlook user and it controls all aspects of my life. I decided to buy a MacBook Pro and the only way to make it work with all the functions I needed was to install VMWARE, Windows and then Outlook. It works well, however the MacBook slows too much and it becomes a burden to do anything else.

    This is the only regret I have at this point for owning a Mac.

    Best,

    Mario

  • Norman

    Where is the problem? I tried Fusion with W7 and Entourage 2008. No way…
    The app crossover is still part of Lion, right? I’ve installed Outlook 2007 in Crossover and it works!