Windows 10 update problems: Why Microsoft’s battle isn’t over yet

Microsoft is overhauling how it delivers Windows 10 updates. But the almost infinite variation of PCs will make that an uphill struggle.

Managing Windows 10 updates will always be a struggle for Microsoft Microsoft is overhauling how it delivers Windows 10 updates. But the almost infinite variation of PCs will make that an uphill struggle.

Microsoft's latest changes to how it manages Windows 10 updates are unlikely to be its last attempts to tweak the process it uses to keep PCs running its latest operating system up to date.  

Microsoft is making changes because the update process has hit a number of snags recently. The idea is that these updates allow new features to be added to Windows 10 on a rolling basis. In contrast to the massive upgrades from one version of Windows to another seen in the past, this move to 'Windows-as-a-service' should allow new elements to be added to the operating system without causing huge upheaval for PC users or IT departments.

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In practice that has not been the case, at least not so far. While Microsoft has made some tweaks to its processes over the past few years, this has not stopped the complaints. Some users have criticised the quality and quantity of updates, and most notably late last year when Microsoft had to pull the Windows 10 October 2018 Update (version 1809) because of a bug that deleted files; it took six weeks before Microsoft started offering the update again.

In a blog post last week, Microsoft's corporate vice president of Windows Mike Fortin acknowledged that its Windows update process can be "disruptive" and set out a number of changes to how updates will be delivered. 

These will include giving users more control over when an update is installed, such as allowing them to block updates for up to 35 days. Microsoft said it will also increase the amount of testing it does on updates and use machine learning to help spot potential bugs. It will also launch a Windows release health dashboard to give users more information on the rollout of updates including problems – open and fixed – in both feature and monthly updates

Steve Kleynhans, research vice president at tech analyst Gartner, said Microsoft's aim is to get new functionality and new security features get into Windows 10 as painlessly and with as little disruption as possible.

"The fact is it's incredibly difficult to do, particularly with an operating system that carries as much baggage as Windows," he said. Microsoft will continue to tweak and adjust the way the updates are done, the tools that are used and the rules around those updates, he said.

"[Microsoft] will constantly be doing that kind of tweaking until they find the right balance and even then the right balance is probably something that's a moving target over time," he said.

Kleynhans said that in some cases Microsoft has under-estimated the difficulties that might crop up when updates are made available to millions of PCs, and also over-estimated the ability of its 'insider program' of testers to spot issues before updates are published.

"I think the reality is that the Windows installed base is an almost infinitely complex set of devices, of an incredible number of variations and no matter how good your representation is with the insider program you're still going to stumble on stuff that you've never seen before when you get out in the field, and I think that's really something they've been bitten by in this case."

With more than 800 million PCs running Windows 10, in all shapes, sizes and ages from many different vendors, accounting for every possible variation is extremely hard.

"At the moment Windows is anarchy to some extent and that's the problem that Microsoft has to deal with, just incredible levels of anarchy that they run into every time they release something," he said.

"Android and iOS were designed from the beginning to be managed in this way, they don't have the level of complexity we've seen evolve in the PC world. A Windows machine carries a tremendous amount of baggage and it's that baggage that causes the problem."

There's also a tension between users – who mostly want new features as quickly as possible, Microsoft – which wants to get new features out, and the IT administrators – who are struggling to cope with much more frequent updates to the PCs under their control.

"IT has to respond to the demands of the users and that means they will have to get used to a much faster cycle time for all software, not just Windows," said Kleynhans.

IT has to be willing to give up some control, Kleynhans said; while in the past, IT departments might test everything in the organisation before rolling out even a security fix, they now feel more confident about the quality of these updates.

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Something similar has to happen with the Windows features updates too, he said: IT needs to scale down testing to what is critical, do pilot testing with smaller groups of users to get a feel for problems, use better information capture and telemetry – and accept the fact that we are in a world that is moving much quicker.

Windows 10 has shown that Microsoft can learn from its mistakes, said Kleynhans. "They are moving in the right direction and things will continue to get better with each release. They are doing the right things to improve where they are. I'm not convinced they have fixed all the issues and I'm not convinced they will ever have fixed all the issues. This is going to be a constantly iterating environment."

Do you think Microsoft is doing enough to improve the quality of Windows 10 updates? Let us know what you think by posting a reader comment below.

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