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Bit by bit, Windows’ reverse compatibility is fading. Here’s how to fight that – and get incredibly old 16-bit software and games like Chip’s Challenge running.

In case you didn’t know: 64-bit versions of Windows can’t run software from the 16-bit era. This isn’t going to be a problem for most people: Windows 3.1, the last 16-bit version of Windows, was released way back in 1992. But if you’ve got an ancient piece of software you want to run on a new computer, are you simply out of luck?

Not completely. Let’s go through your options for running 16-bit Windows software on a 64-bit computer.

I’m committed to preserving the fading games of yesterday The Fading Games Of Yesterday, And How We Preserve Them [Feature] The Fading Games Of Yesterday, And How We Preserve Them [Feature] What is your favorite video game of all time? If you’re in your twenties, or older, there’s a good chance that you answer to this question isn’t a recent title. It may be a classic... Read More , so I’m going to use legendary puzzle title Chip’s Challenge as my example (mostly because my wife Kathy wanted to get it working on her laptop).

There are two main ways to get your software running: setting up something like a virtual machine, or finding an alternative version of the software you want to run. Let’s go through both.

Path 1: Virtualization or Emulation

As I’ve said: 64-bit versions of Windows can’t run 16-bit software. What I didn’t say is that you can set up your computer to run older versions of Windows, all in its own window. It’s called virtualization; here’s how to set it up.

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Windows XP Mode

Microsoft offered Windows 7 users something called XP mode, which gives you a virtual version of Windows XP you can run on your computer. Even better: it’s a 32-bit version of XP, meaning it’s capable of running 16-bit games.

My colleague Chris explained how to use XP Mode in Windows 8 Forget the End of Life Woes: Windows 8 Has an XP Mode Forget the End of Life Woes: Windows 8 Has an XP Mode Windows XP mode is restricted to Professional versions of Windows 7. But there's a way to get Windows XP Mode running on Windows 8 anyway. All you need is a computer running Windows 8. Read More , so check out his tutorial for complete instructions.

Setting Up Your Own VirtualBox

If you’d rather use an old Windows CD you already own, I’d recommend checking out VirtualBox. This software lets you create a virtual computer using any installation disk – we explained how in our unofficial VirtualBox manual. Get a 32-bit version of Windows running and you’ll be able to run your 16-bit software in it.

Get Windows 3.1 Running In DosBOX

This one’s a little convoluted, but I thought I’d include it. We’ve shown you how DOSBox can get old DOS software to run How To Get Old DOS Computer Games To Run On Windows 7 How To Get Old DOS Computer Games To Run On Windows 7 Read More , even without mounting drives Run Old Games In DOSBox Without Mounting Drives Run Old Games In DOSBox Without Mounting Drives Tired of mounting drives in DOSBox every time you want to run an old game on a modern Windows machine? With a little trick you can play your game without wasting time mounting drives. Read More . What we didn’t tell you: Windows 3.1 is a piece of old DOS software, and you can run it in DOSBox.

chips-challenge-dosbox

Yep, that’s Windows 3.1 running in DOSBox – running Chip’s Challenge. Mission accomplished.

Read this tutorial to find out how you can get this working yourself, but be warned: you’re going to need an old version of Windows 3.1 in order to do so (it’s ancient, but sadly not freeware).

Wine (Mac & Linux Only)

It’s easier to get 16-bit Windows software working on Linux or Mac systems than it is on Windows. This is because of Wine, a software compatibility layer that gives Mac and Linux machines the ability to run Windows software.

chips-challenge-wine

It’s ironic, but if you depend on reverse compatibility with really old Windows software, you probably shouldn’t use Windows. Now you know.

Path 2: Find Another Version

Does Virtualization seem too complex for you? Your best bet may be simply searching for a 32-bit version of the program you need to run. It takes a little digging, but for most software it’s possible.

Let’s use the example of Chip’s Challenge, and point out a few 32-bit alternatives.

Tile World 2

This is a remake of Chip’s Challenge that comes bundled with a number of free puzzles. It’s also capable of opening the original puzzles – all you need to do is copy the .dat file from the original game. You’ll notice there’s a different look:

tileworld-default

If you don’t like this, you can grab the original tile set and use that, if you want. I found them on the Chip’s Challenge Wiki.

tileworld-custom-tiles

Just like that, we have a very close approximation of Chip’s Challenge up and running on a 64-bit machine.

WebCC

I’ve shown you classic operating systems you can run in your browser 4 Classic Operating Systems You Can Access In Your Browser 4 Classic Operating Systems You Can Access In Your Browser Ever wonder what the operating systems of the past were like? Find out now, online, without the need to install anything. You can try Windows 1.0, Mac System 7, Amiga OS, and DOS – along... Read More , but at this point most classic games and programs can be found online one place or another. Chip’s Challenge is no exception.

webcc

The art’s a little different, but it works. Enjoy.

What 16-Bit Software Do You Still Run?

I want to know: is there any 16-bit software you’re still using for actual work? What is it? Or, if you’re mostly using this tutorial for playing old games, let me know which ones you’re playing.

Oh, and that DOSBox screenshot above? Getting it was even more convoluted than I let on.

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