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How should you feel about the new Microsoft upgrades schedule?

Much has been made of Microsoft's solemn pledge to deliver new upgrades to its operating systems every year to 18 months. What should you make of this promise?

It's really a mixed bag. There are some good arguments in favor of this new rapid cadence for Microsoft upgrades and new releases out of Redmond.

If a feature you want is in a release that gets to you faster, you are happy with the increased pace. You had to wait five years to get

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Hyper-V from Windows Server 2003. Getting DirectAccess without tearing your hair out took four more after that. Being able to run deduplication on your data volumes was four years from 2008, too. Do you really want to wait that long for new features, especially those with low-effort but high-impact changes? Wouldn't it be nice to at least have the chance to take advantage of those new capabilities, even selectively?

Having the option to upgrade more quickly means that skipping a release no longer puts you years behind the technology curve. Many organizations are still running Windows Server 2003 and skipped the 2008 wave of products, meaning the technology running on their servers is missing at least a decade of innovation. There is a lot of value in stability and working servers, but there have also been huge advancements in technology in the last ten years since Server 2003 was released. Only two major releases have happened in that time: Windows Server 2008 and now Windows Server 2012. Having the major releases come more quickly gives you more opportunity to select a time to upgrade that makes more sense for your organization.

You do not have to adopt every release. At a recent Microsoft briefing, the common refrain was, "No one is being forced to move to Windows Server 2012 R2." And that may be true from a couple of perspectives. There are so few code changes to the kernel and the plumbing that compatibility should not be an issue. Where Windows Server 2012 Gold ran, so will R2. If you're busy, skip R2 or R3, or run Windows Server 2012 R2 and skip Windows Server 2014 (or 2015). Microsoft would argue that you do not have to be a serial adopter, although I am sure the company would love for you to be one.

Even with these arguments, there are some valid arguments against this new sequence of Microsoft upgrades.

Support lifecycles are trimmed for their existing length, which most enterprises are already accustomed to. Windows 8.1 and Windows Server 2012 R2 are considered service pack releases that do not extend the original timeline for support as set out by Microsoft's standard lifecycle calculations. For example, if you did upgrade to Windows 8 right around when it first came out, you have mainstream support for about six years -- until Jan. 9, 2018. But if you upgrade to Windows 8.1, you still only get until Jan. 9, 2018, and you have to upgrade to 8.1 to maintain that date. Otherwise, you basically get shut out on Oct. 18, 2015 or, as the policy states, "two years after the general availability of the Windows 8.1 update." It's always possible that Microsoft will amend these dates, but the move is generally away from the decade-plus support lifecycle Windows XP enjoyed and more toward narrowed windows of supportability.

Migrating to new versions takes more time. Many large organizations are still partially through their migration from Windows XP to Windows 7. It's hard for the Windows 8.1 release now to be compelling for these businesses when they're still moving to a release that first came out in 2009. In fact, some smaller businesses are even moving some of their workloads over to Windows Vista just to maintain support and hotfix availability as Windows XP support sunsets; those businesses are not in a financial position to make the hardware expenditures required to run Windows 7, Windows 8 or Windows 8.1 in a decent way. Even if you intend to adopt every other new release, you're essentially in a constant state of upgrading, migrating and moving, even as your hardware expenses have tended to stabilize in terms of performance and productivity per dollar.

Quality has been slipping. Everyone who's experienced Windows 8 knows that it feels unpolished in many areas, especially when compared with Windows 7. ZDNet's Mary Jo Foley noted from insider sources that Microsoft "announced internally that the quality metrics for Windows 8.1 were back in line with those of Windows 7," suggesting Windows 8 did not live up to that bar.

Overall, I am neutral to slightly negative on this Microsoft upgrades pace. One-year release cadences may make sense for Microsoft's product teams, and it may be a way to solve the company's own issues with being slow to market and mitigating a sense of being "behind the times" in some businesses. But I've yet to meet any enterprise that has jumped up and down screaming for the last 15 years that they need new releases every 12 or 18 months. I suspect we'll see Microsoft slightly extend these timeframes, with perhaps three years between major releases and 18 months between point updates, but only time will tell.

About the author:
Jonathan Hassell is an author, consultant and speaker on a variety of IT topics. His published works include RADIUSHardening WindowsUsing Microsoft Windows Small Business Server 2003 and Learning Windows Server 2003. Jonathan also speaks worldwide on topics ranging from networking and security to Windows administration. He is president of 82 Ventures LLC, based in North Carolina, and is currently an editor for Apress Media LLC, a publishing company that specializes in books for programmers and IT professionals.

This was first published in October 2013

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