When it comes to Windows Update, Microsoft has had it rough over the last few years, reputationally speaking. At one point it seemed to us that the word “Borked” (a slang term used to describe something that fails to work due to the negligence / incompetence of its instigator) had been invented for the exclusive use of describing the Windows Update process. Before we all jump on this bandwagon though, let’s have a little look back at the history of Windows Update so that we can get a little context on this, and understand exactly what Microsoft has been trying to achieve over the years. It’ll explain a lot about where we’ve come, and why we are where we are!

A brief historical of Windows Update

In the very early times, (think 1992 and Windows 3.1) you kind of got what you got! If there was a bug or feature missing from Windows, the choices were to either wait until the next version (3.11 in this case) or obtain third party software to address the issue(s). Given that users were expected to pay for subsequent versions, along with, generally, all third party software, this wasn’t a financially advantageous position for them to be in. However, things were about to improve, slightly!

With internet usages fast gaining speed in 1995, Windows 95 allowed users to download fixes (also known as “patches” from Microsoft’s website. This was usually to fix things that were “broken” (like the infamous “Microsoft Shutdown patch” which allowed Windows 95 machines to finally shut down instead of hanging on the “cloud” screen) as opposed to being able to add new functionality. Moreover, users had to know what they were looking for, and install it themselves at a fairly low level.

With the introduction of Windows 98 in, you guessed it, 1998, users were introduced to a Windows Update web application that allowed them to see all applicable driver updates / fixes in one place. It was a total revelation.

Subsequent versions of Windows only built on this, by doing away with the web app in favour of an inbuilt system that not only replicated everything from before, but also introduced security fixes (as “holes” were found) along with functionality tweaks and updates.

Present Day

Windows 10 is by far the most evolutionary operating system, bringing security updates on an “as and when” basis and then, roughly every 6 months, a much larger “Feature Update” that focuses on, as the name suggests, new features. This keeps Windows technologically current from a user interface point of view, without the need for users to fork out for an entirely new version. However, since the Feature Updates are major in scope, they often “feel” almost like installing a new copy of Windows.

Feature updates largely follow the format; year and month . To sum up:-

Sadly, too, there has been multiple occasions in Windows 10’s “Update past” when Feature Updates have damaged what was already installed, to the point of, in the case of the 1809 Update, actually losing user’s files.

So what should I do?

We do understand that the fear of losing production time or even files can dissuade users from updating Windows but really, the potential upsides for it far outweigh the (relatively infrequent) negatives as a policy of installing updates ensures that you’ve got the latest windows security fixes in place.

There is no fully right answer to the above question, as it depends on the use of the machine in question. Your firm might adopt a specific policy based on;

1. Updating a small number of machines at a time within any particular functional group, before moving on to others when those updates are complete. This would prevent the risk of knocking out entire departments at a time, Payroll for example!
2. Updating machines regularly for fixes, but WAITING for a set time (say, 2-3 weeks) before applying the larger Feature Updates. This would give time for any installation / operational bugs to be identified and ironed out
3. Trialling updates on spare machines, or ones deemed to be of lower priority, to ensure that the organisation’s systems are in no way compromised,

Update Time

When it comes to the actual application of the updates / features, there are two prior steps that will go a long way toward making the process as painless as possible;

1. Take a backup first. This is standard. No ifs, buts, or maybes. If you have stuff you don’t want to lose, back it up.
2. Get a System Restore point. This is a special feature of Windows 10 to allow you to roll back changes to an earlier time if there is a problem following an installation of any kind. To do this, go into the Settings App, and type “System Restore” in the search box, then click on “Create a Restore Point”

Once you’re sure the above is all done, you can go ahead and perform the update. Here, though, is where you might get to what is absolutely the most commonly occurring problem associated with this procedure; not reading the screen!

When a modern Operating System (read, Windows 7 or 10) is performing an update, there will usually be a message displayed to the effect of “Please do not turn off your computer”. Please, HEED THIS WARNING! No matter how long that message is on screen for, DO NOT POWER OFF.

So often we get users who have ignored this message and decided to power off their PC / laptop during an obviously critical phase of the update process. Kind of like getting out of a car before it has come to a complete stop, an inevitably painful experience. The same can be said of Windows Update and on many occasions, users who have done this run into trouble when trying to start Windows on the next boot. In such circumstances, professional help is often required restore the machine back to rights.

To reiterate, in case this blog has not made it absolutely clear, DON’T POWER OFF YOUR COMPUTER DURING AN UPDATE. You can’t say you haven’t been warned!

An Even Better Way? Maybe.

Following the above steps should leave you in a reasonably good position to judge when to perform your Windows Updates, but there is potentially an even better way of doing it if you’re running a modern Windows Server in your Network; WSUS, or “Windows Software Update Services” is a way to centralise the Windows Update policy in your organisation. It provides the following key benefits;

1. The Administrator gets to approve updates before they are rolled out to the Workstations
2. The Administrator can decide who gets what, and when
3. The Server stores the update files centrally and users update from there rather than the internet, meaning faster updates when bandwidth is limited and in any event, less bandwidth overall
4. The Administrator can easily see which machines have not yet been updated

Whilst the benefit of (3) is reduced with the advent of Windows 10’s Delivery Optimisation feature (which allows Windows 10 to download updates from other Windows 10 machines) the other benefits are still marked, and highly worthwhile for Networks with large numbers of machines. The break-even point for WSUS is probably 20-30 machines. Networks with fewer than this will still see the benefits of course, but whether the initial labour investment is worth it would be down to the firm’s decision maker to conclude.

Summary

Windows Update is good, and should be used, but make sure you have the backups and restore points in place. Oh, and don’t turn off the machine during the update; we may have mentioned that earlier!

If you’re in any doubt as to how best to implement a Windows Update policy or WSUS in your organisation, please feel free to contact us and we’ll go through it all in our usual friendly and professional manner!