The title might suggest that we’re a little behind the curve with this, but there’s a very good reason for asking this question now.

Microsoft has been offering an upgrade to Windows 10 free of charge and has made the process (relatively) painless for most users. They have always said that this was a limited offer, but have now stipulated an end date of the 29th July 2016.

After that date they have indicated that they plan to charge for the upgrade.

There used to be a school of thought that said you should waiting for the first ‘service pack’ of an operating system before installing it, on the basis that you didn’t want to be a beta tester for Microsoft. The world of security updates and system vulnerabilities made this sort of thinking archaic (and possibly dangerous) years ago, but if this is still your view then Windows 10 recently had it’s ‘big update’ and I think we can say it’s safe to move forward now.

So should you upgrade?

Yes, generally, but it’s worth answering a few questions first.

If you are running Windows 8 or Windows 8.1 then you should upgrade. Both of these operating systems use the same driver sets as Windows 10 but are just less pleasant to use. Upgrading will make your machine feel nicer.
If you are running Windows XP or Windows Vista, then don’t upgrade - throw the machine away and buy a new one. These operating systems are insecure and should not be on your network.
The vast majority of you will have Windows 7 machines that you could upgrade. Before you make your decision, take the following into consideration.

Will you want to upgrade at some stage?

If yes, then you should try your upmost to upgrade before the deadline. Otherwise accept that you will probably retire the machines with Windows 7 and replace them.

Do you run something that can’t run on Windows 10?

This is the biggest consideration. You need to check all your major applications are Windows 10 compatible (such as accounts software, manufacturing systems etc). Remember - holding on to old software in your organisation often ends badly. Use Windows 10 as a catalyst to identify systems that need to be upgraded.

Do you have devices that are incompatible with Windows 10 ?

The Windows 10 driver set is pretty comprehensive, but if you have very old printers, scanners, plotters or any industry specific hardware then you need to check compatibility with the manufacturer (usually through their website).

Windows 10 is a faster operating system. It’s different from Windows 7 but it’s not worse. Microsoft will not change their mind and make Windows 7 again, so at some point you will need to move. It’s just whether you do this for free.