Microsoft's faster Windows 8.1 updates place an enormous burden on large IT shops, where administrators must update Windows clients and servers together but don't have time to test the rollouts properly.
In addition, Windows 8.1 users must be current on updates to receive future security and nonsecurity updates. These client rollouts are tied to other Microsoft products, including Windows Server 2012 R2, Visual Studio, Windows Intune and Azure.
The fast-moving train connecting multiple platforms leaves IT with too little time for large companies to properly vet updates, industry experts said.
"It was hard to deal with three-year releases, harder still when one-year updates came, and now the six-month cadence is a big problem," said Wes Miller, an analyst at Directions on Microsoft, an independent consulting firm in Kirkland, Washington, during a Windows Roadmap update webinar last week.
"Be prepared to test rapidly," he said.
Today, most companies use Windows 7 and plan to stay on it for some time, so the faster Windows 8.1 update cycle has had a minimal effect so far.
Be prepared to test rapidly.
Wes Miller, Directions on Microsoft
However, "this would give many organizations another reason to avoid implementation of 8.x, so I think it could backfire on Microsoft," said Matt Kosht, an IT manager at a Michigan utility company.
For companies subject to regulatory requirements, application testing is necessary before an update rollout. These IT shops find Microsoft's new cadence particularly troublesome.
"Microsoft wants to get Windows to behave like a cloud service, but the updates don't 'just work,' especially when it comes to third-party software," Miller said.
The faster cadence is sure to pose a big challenge for some software providers, including antivirus vendors. "Many haven't even kept up with new releases of IE beyond IE8 or support 64-bit releases of Windows, much less embracing Windows 8.1," Kosht said.
Microsoft Windows 8.1 update challenges
Servicing Windows is not easy, but the most recent patch is particularly complicated, with several issues along the way, Miller said. Earlier this month, a Windows 8.1 update bug interfered with Windows Server Update Server and prevented Windows 8.1 from scanning the corporate update service.
"We are seeing a big change in how updates are delivered, trying to sync with Windows Phone and address concerns for non-touch devices," Miller said in the webcast. "It's messy. I wish there was a broader enterprise preview for testing."
Other industry observers agreed that Microsoft is making life difficult for IT shops that need time to properly test Windows 8.1, particularly those that must comply with state and federal government regulations. However, they added that users have known for some time that this accelerated pace was coming.
"Those who have deployed the latest version [of Windows 8] should have expected this new tempo to releases because it has been part of the conversation from the start," said one longtime Microsoft insider.
"Microsoft has set the standard in that realm since they formalized the lifecycle policies back in 2006," he said. "But on the surface this appears to ditch that."
Even if users already had Windows Server 2012 in place, they must upgrade to move up to R2.
"It will take time and money because going to Windows Server R2 is not a free upgrade, and you will likely have to upgrade the hardware in some cases," Miller said in an interview following the webcast. "But you won't have to upgrade the entire hardware infrastructure, just those servers dedicated to being a domain controller focused on file services."
Fast Windows updates: The new normal
Some IT professionals don’t see faster updates as a major problem.
"If they are imposing Windows Server 2012 R2 on you, that is not good, but I don't think it will necessarily kill people's incentive to go to Windows 8.1 Update because that is something they won't be dealing with for at least a year," said Mike Drips, a solutions architect at WiPro Technologies Inc. in Houston.
Others focus on the upshot. The frequent updates -- such as improved mouse and keyboard support, disabling Modern/Metro behaviors on non-touch devices, and IE11 Enterprise mode -- will give Windows 8.1 a better chance of making it to the enterprise desktop, Kosht said.
The faster release cycle isn't much of a change, since Microsoft releases critical patches every month, he added.
"Once IT retools to keep up with the six-month cycle, the incremental changes between updates will be small enough to test and will be just part of the 'new normal,' continual software updates," Kosht said. "If you compare Windows to say iOS or Android, those OSes are getting significant updates in even shorter time frames."
In addition, no matter how troublesome patches are, faster updates are necessary for security.
"Patch management and testing has been and always will be a daunting task for IT departments," said David Reynolds, systems manager at Rhode Island Blood Center in Providence, R.I. "We all dread perusing the list after Patch Tuesday, which inevitably has to be tested to the best of our abilities for third-party software compatibility."
But, "IT testing and patching have to move somewhat swiftly," he said. "Six months ... is an eternity in the realm of IT time. Security holes are exploited in hours after [they are] published, let alone months."
Meanwhile, Windows 7 and 8 are both stable, so IT shops may want to remain there as long as possible to ensure stability, Miller said. But Windows 8 support is timelined; IT has just over a year to update to 8.1 at least.
"You can't stay on 8 forever," Miller said.
Slow the Windows update train
To stop Windows 8.1 client updates from dictating Windows Server updates, IT must decouple clients from servers. This will make the most sense in bring your own device (BYOD) scenarios, where end users have a choice in updating their systems, and corporate server updates won't be forced before IT is ready, Miller said.
In addition, OMA device manager or Windows Intune is recommended instead of Group Policy for unmanaged BYOD systems -- another sign of Microsoft's momentum toward management as a service, Miller said.
"Group Policy isn't dead, but it isn't getting the love that it once was," he said.
Since Windows 8.1 Update is required to receive future updates, IT admins should determine where problems may occur.
Making sure updates are sound is important to IT pros, but it's either a blind spot Microsoft is ignoring, OK with or unaware of, Miller said during the webcast.
"If you have a good [Microsoft] contact, keep emphasizing to them that the cadence and lack of clarity around when updates come and inability to test makes it difficult to use Windows," Miller said.
Microsoft declined to answer questions regarding enterprise customer concerns around the updates. Instead, a spokesperson said the company is monitoring the release, discussing this new approach to servicing with enterprise customers and listening to their feedback regarding managing the deployment timeline.
Microsoft recently extended the timeframe for enterprise customers to deploy these new product updates from 30 to 120 days, aligned with the Aug. 12 update cycle.