How does “Rapid Release Cycle” square with Upgrade Procrastination?

I can’t help but notice when I’m teaching courses on Windows Server 2012 that there’s a good number of people out there in large organizations that are still running Windows Server 2003. We all know that the desktop operating system statistics say that more than 35% of desktops are running Windows XP even though it has less than a year left of support. If we were looking at the percentage of servers running Windows server operating systems, I’d guestimate that the number might be even higher. So that’s the first part of this puzzle: there’s still a very large number of people running Windows Server 2003 in workhorse roles.

The other part of this equation is Windows Server 2012 R2 will be RTMing in a couple of months even though I’m betting only a fraction of organizations have moved to Windows Server 2012. Microsoft has stated that it’s moving to a rapid release cycle. The next version of Windows Server after 2012 R2 is probably already coming down the pipe.

There’s a disconnect here. A large segment of the market hasn’t moved their server infrastructure from Server 2003 and yet the release cycle is getting faster. It’s not as though there haven’t been good alternatives – whatever the reception of Vista, Windows Server 2008, Windows Server 2008 R2 and Windows Server 2012 have all been widely praised operating system. A substantial number of people aren’t migrating to newer operating systems because …

… when I ask people who are still running Server 2003 why they are still running Server 2003 there tends to be an embarrassed shuffling of feet and some mumbled dialog about getting around to upgrading one of these days …

Will the new server operating system rapid release cycle exacerbate or cure upgrade procrastination? The new release cycle is fantastic for those that want to run at the cutting edge, but I think that there are a large number of systems administrators out there who are less than enthusiastic about it. They’ve already procrastinated about going from Server 2003 to a new version, realizing that they’ve not only got to get back on the hamster wheel but stay on it isn’t necessarily going to drive them to new heights of motivation.