Computer hardware changes rapidly. Know what you should upgrade on your PC depends on how you use it. Games often require the latest available pieces, but older software sometimes behaves differently.
There’s no worse feeling than updating your operating system only to find that your favorite programs no longer work. Windows 10 compatibility mode can help you get your software working again.
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Why is old software broken?
Before looking at how to recover old software, you should learn about why they might not work with Windows 10. While there are a large number of potential problems with old software, most of the time. All have the same problem:
- Outdated dependencies – software that depends on old programs and libraries that are no longer available in Windows 10
- 16 bit program – Windows 10 is 64 bit and does not support 16 bit programs * 32 bit works fine though)
- DOS – Older programs and games designed for MSDOS do not run in Windows, as it only emulates a small portion of the DOS system for a Terminal window
- Guard – Exploits and backdoors for constantly changing programs and outdated software may be rejected because of security risks
These and many other problems can prevent old software from running. Keeping legacy software alive is a topic many people are passionate about and there are online communities devoted to expanding products beyond officially end of life.
How to run software using Windows 10 compatibility mode
If you’ve tried to install an older piece of software and just found it refuses to run, you have several options. The first is to use the automatic compatibility checker to match the software with different modes to get them up and running.
- Right click on .EXE file and select Characteristic
- Under Compatibility tab, click Run the compatibility troubleshooter
- Wait while Windows scans the program
- Option Try the recommended settings

This will set up the program to work with whatever settings Windows 10 deems best. If it still won’t launch, repeat the process, this time choosing Troubleshooting program at the last step to launch the interactive wizard.
Program Compatibility Troubleshooter works best on newer software. But if you know exactly what software the program is meant to run on, then you’re better off using manual mode.
How to manually select Windows 10 compatibility mode
If you’ve tried the previous steps and they don’t work, there are other options to try before giving up. You can manually select which system to use with Windows compatibility mode:

- Right click on .EXE file and select Characteristic
- Under Compatibility click Run this program in compatibility mode for: check box
- Select the version of Windows the program is written for
- Click ALRIGHT
Now, whenever that program is opened, Windows 10 will try to run it through shimsSpecial software designed to bridge the gap between old and new operating systems.
What to do when Windows Compatibility Mode doesn’t work
Windows 10’s Compatibility Mode does a good job of running a lot of older software, but sometimes it comes across as too old or outdated to run. There’s no easy fix in these cases, but that doesn’t mean it’s impossible.
There are some other options for running legacy programs, but they are a bit more adventurous.
Run older versions of Windows in a virtual machine
A virtual machine is an entire operating system that runs in a sandbox program on your computer. It’s a great way to try other operating systems and Linux distribution.
The benefit of a virtual machine is that it can emulate old hardware perfectly. This way, instead of trying to get Windows 10 to run programs for older operating systems, you can running Windows XP natively in a virtual machine.
This comes with a number of advantages, although perhaps the most important is the separation between your modern system and older software, eliminating any possible security issues that the software has. can cause.
Run DOS software with DOSBox
Before Windows, all software ran under the DOS operating system (commonly known as MSDOS). There is no compatibility between modern versions of Windows and DOS, but there are options to run programs through emulators.

You can install software in a virtual machine, but DOSBox is a much easier option. It’s completely free, open source, and designed to support a wide range of legacy games and software across a variety of platforms, including Windows and macOS.
Build computers with old hardware
For the ultimate hardcore approach, you can build a dedicated computer to run the operating system of your choice. It sounds extreme, but that’s exactly what YouTuber MattKC did.
As the video shows, this approach is full of bugs and not for the faint of heart. However, if you want a challenge, the thinking behind building an old PC is solid. After all, large amounts of government, medical, and military software still run on older machines to this day.
However, whether you think it’s a good thing or not, is subjective.
Old Software, Modern Hardware
Keeping old software alive can be a passion or maybe you need it for your business. Either way, Windows 10 has some options for keeping old programs alive.
If you run Windows 7, you can find XP Mode useful for the same reasons, and Windows 8 users will find a similar Windows compatibility mode built into their operating system.