Why does my HP Pavilion laptop tell me that Windows 10 is up to date, but at the same time tells me I’m running a version that’s nearing the end of support, and recommends that I update to the most recent version? Frank

First, some background. Microsoft used to provide new versions of Windows every three or more years, and support them for 10 years. Examples included Windows XP and Windows 7. They didn’t change unless Microsoft released a service pack update, such as Windows 7 SP1.

When it launched Windows 10 four years ago, Microsoft switched to delivering “Windows as a Service” (WaaS). Now the operating system is updated every month, at no charge, with two “milestone” releases each year. These are named after their intended release dates, such as Windows 10 1809 and 1903. (The March update, 1903, was actually released in May.)

Thanks to WaaS, there are no more expensive “big bang” updates, which used to cause large organisations enormous pain and left some of them clinging to obsolete versions of Windows for more than a decade. Smaller, more frequent updates are much easier to handle, especially using tools such as WSUS (Windows Server Update Services), SCCM (System Center Configuration Manager) and WUfB (Windows Update for Business). They are a bit of a pain for some home users, but Microsoft is trying to alleviate any problems.

With WaaS, Microsoft also changed its support system. It now has a Modern Lifecycle Policy where basic versions of Windows 10 are only supported for 18 months. You have lost the 10 years of support, but your support now continues for ever, as long as you keep installing new versions of Windows 10. In reality, “for ever” means for as long as your device can run them.

The net result is that Microsoft is still supporting at least three versions of Windows, but the three will usually have been launched about six months apart, instead of three years apart.

Where you are

You are, I deduce, running Windows 10 version 1803: this was released on 30 April 2018, and reaches the end of its supported life on 12 November 2019. So Windows Update is telling you, correctly, that this version is up to date.

However, you have failed to install either of the two latest milestone releases, 1809 and 1903. You therefore have an up-to-date version of an out-of-date version of Windows 10. Your current version does not need updating, it needs replacing. This is what you should do.

You are in much the same position as someone who is still running an up-to-date version of Windows 7, having skipped later releases. The main differences are that the timescales are much shorter and the upgrades are now free.

Microsoft would like everyone to be on the same version of Windows, and it would not be economic to support 10 or 20 different versions. It is therefore using the end of support – and the end of security fixes – to push users into updating their systems, even though the Windows 10 Enterprise version of 1803 will be supported for another year (until 10 November 2020).

These PCs are less of a burden because large organisations use tools such as WSUS to update thousands of PCs, rather than each one downloading the code separately. Either way, Microsoft must still be producing security fixes for 1803; it just won’t let you have them.

Upgrade strategies

With WaaS, not everybody gets the code at the same time, as you might expect. Instead, the task of updating more than 800m PCs is spread over many months.

A few million people want the latest version, even if it isn’t finished. They join the “insider ring” of beta testers, who look for bugs before the operating system is released to a wider audience. Some are what Microsoft calls “seekers”: they check manually for updates and install them as soon as they become available. Most people just ignore new versions until they are reminded to install them, or – if they really are not paying attention – the installation is practically under way.

In general, it’s safer to install milestone updates later rather than sooner. If you upgrade to version 1903 now, you will get a version that has had months of testing, and that has already been installed on hundreds of millions of PCs. If you wait for the “fall version”, currently called 19H2, then you will get code that hasn’t been as thoroughly debugged. Also, it will be a bigger leap from 1803, and big leaps are inherently riskier than small ones.

You don’t have to be on the current version of Windows 10, where some new features may introduce a few new bugs. However, it’s a bad idea to fall two or three versions behind.

Update problems and solutions

The mass upgrade process depends on a lot of machine learning based on feedback from telemetry. The PCs that seem easiest to upgrade correctly are offered updates before the ones that look trickier. As bugs are found and fixed, updates are offered to more and more PCs.

Updates are sometimes suspended for various reasons. It happened to some PCs that had not been patched for the Meltdown and Spectre vulnerabilities. With 1903, some users were put on hold because their PCs were running an outdated Intel Rapid Storage Technology (RST) driver. In my case, the warning went away and Microsoft installed a Microsoft driver. For the reader who wasn’t so lucky, it should have been fixed by the KB4512941 update on 30 August.

Update attempts can also fail because your PC does not have enough storage space. You need enough room for the version of Windows that is running, the version you have downloaded, and a security copy of the old version of Windows 10 in case you need to roll back a failed upgrade. This backup is now deleted after about 10 days; it used to be about 30 days.

Windows 10 should upgrade correctly if you plug in an external hard drive – that has worked for me – or provide other storage space. If that doesn’t work, the solution is to download a copy of Windows 10 and the free Media Creation Tool, create installation media on a USB memory stick or DVD, then install a new copy of Windows 10. Obviously, you must back up your data first.

Otherwise, you may be able to solve update problems by downloading the Update Assistant.

You can also contact Microsoft support via the “Get help” link on the right hand side of the Windows Update page in the Settings (cogwheel) app. I tried it once, got instant help, and it was helpful. The Microsoft Support web page for Windows 10 offers further options including “call me back”, “schedule a call”, and “ask the community” (by posting in the support forum).

Sometimes it helps if you have checked your PC’s telemetry using the Diagnostic Data Viewer app available in the Windows Store. Alternatively, look at the Problem Reports page in the Security and Maintenance section of the old Control Panel, or the Event Viewer.

Better updates

The current 1903/May 2019 version of Windows 10 is a bit more flexible. You can click a pause button to “pause updates for 7 days” or skip down to “Advanced options” and pause updates for up to 35 days. You can pick a date when you want to resume, which is useful for business trips and holidays. After 35 days, you have to install some updates before you can pause it again.

With the forthcoming 19H2/1909 version, Microsoft plans further changes. In particular, it will try using the same trick as major browsers: install feature updates without turning them on. This introduces an exciting new three-letter abbreviation: CFR (Controlled Feature Rollout). Microsoft defines this as: “A method to progressively rollout new features by gradually increasing the audience in a controlled manner.” In other words, every PC will get the same updates, but new features will be turned on gradually while telemetry checks that they are working correctly.

According to Microsoft’s John Cable, who is in charge of Windows servicing and delivery, the aim is to make the twice-yearly updates more like the monthly updates. In the same blogpost, he said: “Anyone running the May 2019 update and updating to the new release will have a far faster update experience.”

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