A Windows update nightmare makes me glad, once again, that I use a Mac

update below:

Microsoft has done it again. With the update of Outlook Social Connector released today - and a nightmare of an experience that has left me completely locked out of Outlook - the company has once again made me glad that I choose to be a Mac, instead of a PC.

In a post last week, I tried to make a point about how lame Microsoft's new product announcements because they always "announce" but then you wait months for those products to become available. The announcement at the center of that post was OSC, an add-on that's supposed to incorporate social networking sites directly into Outlook.

I took a few slams from readers (and even a colleague) for not recognizing that OSC had actually been released in beta back in November, with an announcement for LinkedIn compatibility. Of course, LinkedIn wasn't available to use in Outlook yet - that was just an announcement, silly. Since November, the only thing available as part of OSC has been Sharepoint.

Today, Microsoft released an update to OSC that included the LinkedIn add-on. The company also "announced" compatibility with Facebook and MySpace - but, as expected, those two aren't "available" just yet.

Not wanting to unnecessarily subject myself to additional criticism, I went ahead and installed the update on a Windows 7 machine I keep handy for such tests. After a reboot, I was ready to rock, hoping to see LinkedIn on the OSC pane within Outlook. Instead, I got a generic error message that didn't really tell me anything other than there had been an error and that Windows would contact me if a solution became available.

Now, I'm locked out of Outlook - even after uninstalling the OSC update. If Outlook were my only access to email and calendar, I'd be really screwed right about now. Good thing I have Mac - and cloud - access to my inbox and calendar.

Frustrated with the experience, I turned to my BTL counterpart Larry Dignan, a Windows user who I exchange PC vs Mac jabs with pretty regularly. Microsoft blogger Mary Jo Foley then joined the conversation, suggesting that I uninstall any previous betas I had installed before installing the OSC update. Hmmm. I don't recall seeing that as Step 1 on the OSC page.

My reply to that: If it were Apple or Google, the update would have just installed over the old version. And it would work, no uninstall necessary.

Argh!

Then, I saw the fine print about 32-bit vs 64-bit and how this was a 32-bit version that wouldn't work on 64-bit. I have to admit, I didn't know off the top of my head whether I was running 32-bit or 64-bit so I had to dig into the control panel to find out. (It's 32-bit.)

My argument: would regular consumers really know this off the top of their heads? I doubt it. But that shouldn't matter. Shouldn't the software be smart enough to read my machine's configuration and determine whether a download is compatible or not. If it is, put that download link out there and let me have at it. If it isn't, then grey out that download link and let's move on. The burden of determining compatibility shouldn't fall on the end-user in cases like this. I tell Larry this and he comes back with this:

Lesson of the day: If you don't know what version of Windows you have, 32 bit or 64 bit, you really shouldn't be screwing around with betas.

And then he tweeted that same message.

OK, point taken. Maybe I'm just not smart enough to own a Windows machine.

Instead, I like to think that, as a Mac guy, I'm actually smart enough to know better than to rely on Windows.

update: A reader posted a link to the official Microsoft Outlook blog that addressed the issue of Outlook crashing. I followed the instructions and was able to get back into Outlook, get the updated Outlook Social Connector installed, as well as the LinkedIn add-on.

I know I've taken a beating from several of you in the talkbacks since this post went live and I wanted to address and clarify a few points.

• I never said this was a work machine, nor did I say it was my primary. It's here for exactly these sort of tests, which means that an Outlook lock-out was unfortunate but not devastating.
• The PC is a 32-bit. I checked so I would know if that was the problem. It was never a matter of me trying to install 64-bit on a 32-bit machine. My point was that end-users shouldn't be forced to check.
• I did read the instructions first. No where on any page did it ever say that anyone needed to uninstall the old version first. In fact, the step-by-step instructions from Microsoft on how to clean your system of the old OSC was very good. Too bad it wasn't included in the first set of instructions. God forbid Microsoft doing something user-friendly the first time around.
• A back-up or data loss was never a problem. I didn't lose emails or my calendar - just Outlook.
• As for the personal attacks against me... well, I'm thick-skinned and pretty much expect some of these sort of comments. For those who commented about the talkbacks being a forum for professional exchanges, all I can say is... I hear ya.