Old Software + Modern OS = ?

Have you ever wondered what the oldest version of Office you could run on a modern Windows operating system such as Windows 10?

How about that old box for Microsoft Encarta that you have?

Maybe not, but this is something that I find fascinating. In this series of posts we will take different large applications and see how they react in the modern world. Microsoft have always boasted backwards compatibility as one of their major selling points of their operating systems over the years, but at what point is too far.


I am an IT professional by trade. Please do not take these posts as evidence or validation for using outdated software in commercial or production environments. No-one should be trusting their business operations (no matter how big or small) on old software. Almost all of this software is no longer supported by the vendor – no longer patched and could break with the next round of updates to descend onto your device. Please keep your IT managers, engineers and helpdesk staff happy by keeping things truly in the modern age. I’d rather fix Office 365 than Works 97. Simply put, this is a bit of fun.

Also although most of the software in this series shouldn’t rely to heavily on hardware, your mileage may vary when it comes to running it. I am always an advocate for using period correct hardware (and operating systems) where possible.

How It Works

All the software covered here I will have as a physical copy. I am focusing mainly on “big software” less so on things such as freeware, shareware, demoware etc.

Each item of software will be tested inside a virtual machine (provided by Oracle’s VirtualBox) with the latest mainstream copy of Windows 10 available at the time. This build will be stated in each post. Some items of software will be revisited to test compatibility with later builds.

The software will be tested to see if it:

a) executes the main application/applications without error
b) basic functionality is working

If either part fails, then I will test various sub-components (if available) compatibility.

I am happy to test certain functionality upon request, leave a comment and I will give it a go – no promises on how quickly these requests will be addressed.

The Software