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Microsoft has a long history of backwards compatibility. It hasn’t always worked well, but that backwards compatibility is always present. The majority of Windows applications will work on Windows 10, just as they did on Windows 8. However, as Microsoft presses forward, some older games and software will become obsolete Remember These? 7 Ancient Windows Programs Still Used Today Remember These? 7 Ancient Windows Programs Still Used Today They say technology advances at an exponential rate. But did you know some programs have been around for multiple decades? Join us for a walk down Nostalgia Lane and discover the oldest surviving Windows programs. Read More .

Applications designed for Windows XP, Windows 98, and even DOS, may cease to function. In this case, it comes down to a game of trial and error. While some games and software can be coaxed into life using Windows 10 built-in compatibility modes, others will require special system tweaks, patches, or emulators.

Before you give up hope, try our tips getting that old application up and running.

Why Is It Borked?

There are a variety of reasons your old game or software may be refusing to play ball with Windows 10.

  • Dependencies on Old Versions of Software — Some software depends on old libraries no longer automatically installed by default.
  • 16-bit Software64-bit versions of Windows 4 Easy Ways to Know If You're on a 64-Bit Version of Windows 4 Easy Ways to Know If You're on a 64-Bit Version of Windows Are you using a processor that supports a 64-bit operating system and are you running a 64-bit operating system? The average off-and-on PC user probably doesn't know the answers to these questions, although they should.... Read More no longer contain the built-in compatibility layer for 16-bit Windows applications.
  • DOS Software — Windows 10, like all versions of Windows since Windows XP, no longer runs on top of DOS. Some DOS programs will still run, but the vast majority — and especially games — simply fail to run.
  • DRM — Antiquated or non-existent DRM solutions that stop applications booting.

How Can You Fix It?

1. Run as Administrator

If your issue is with a Windows XP program, the first thing to try is running the application as an administrator. During the Windows XP era most users were typically administrators. This isn’t always the case with Windows 10, as Microsoft attempts to shore up security. Applications were coded with the assumption they had administrator access, and would fail if not.

red alert run as administrator

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Head to the application executable or its shortcut, right-click, and select Run as Administrator.

2. Program Compatibility Troubleshooter

If right-clicking the application fails to work, we can try to let Windows 10 make its own decision about compatibility settings. Windows 10 has an integrated Program Compatibility Troubleshooter that helps to “detect and fix common compatibility problems.”

Use the Start menu to search for run programs. Select the best match to open the troubleshooter.

run programs made for previous windows versions

Click Advanced. Then select Run as Administrator. Click Next.

run program run as admin

The troubleshooter will now scan your system for potential compatibility issues. If your application isn’t listed, select the Not Listed option, and select Next.

run program not listed

You’ll have to browse to the executable or shortcut. I’ll be testing one of greatest football management games ever made: Premier Manager 98.

run-program-browse-to-file

Continue by selecting Try recommended settings.

run program use recommended settings

Once the settings have been applied, test the program. As you can see, the program now works, albeit notifying me that I need the original CD-ROM. Press Next.

premier manager 98 compatibility test

Compatibility Fail

The troubleshooter will now ask you if the fix was successful or not. Selecting Yes, save these settings for this program will close the troubleshooter. Selecting No, try again using different settings will open an additional dialogue containing the following options:

  • The program worked in earlier versions of Windows but won’t install or run now.
    • Example: The setup program won’t begin.
  • The program opens but doesn’t display correctly.
    • Example: Wrong colors, size, or resolution.
  • The program requires additional permissions.
    • Example: Access denied errors appear, or the program requests administrator permissions to run.
  • I don’t see my problem listed.

Make your selection based upon the results of the test we ran in the previous section. The examples listed should help you understand which option is right for your application. However, it might take a combination of fixes to get it up and running, so don’t lose hope at the first hurdle.

run program more problems encountered

I Drive a Manual

You don’t have to use the troubleshooter. You can access compatibility options through the application’s Properties. Browse to the application you wish to troubleshoot. Right-click and select Properties from the context menu.

premier manager 98 properties option

Select the Compatibility tab. Use the Compatibility mode option to run your application in a previous version of Windows. Furthermore, you’ll find compatibility settings for Reduced color modes, Run in 640 x 480 screen resolution, Disable display scaling on high DPI settings, and Run this program as an administrator.

premier manager 98 compatibility properties

The automated troubleshooter offers the same options. When you’re finished, press Apply, then OK.

compatibility properties run in windows version

Keep in mind that these changes only affect your user account. If you’d like to apply the compatibility settings changes for every user, use the Change settings for all users button.

As with the automated troubleshooter, this will be a process of trial and error.

3. Unsigned Drivers

64-bit Windows 10 uses driver signature enforcement. This requires all drivers to have a valid signature. Conversely, 32-bit Windows 10 doesn’t normally require driver signing, though versions of Windows 10 running on a newer PC with UEFI How to Update Your UEFI BIOS in Windows How to Update Your UEFI BIOS in Windows Most PC users go without ever updating their BIOS. If you care for continued stability, however, you should periodically check whether an update is available. We show you how to safely update your UEFI BIOS. Read More do require signed drivers.

Driver signing helps with security and stability, ensuring malicious or unstable drivers don’t slip through the net. It isn’t perfect, but certainly helps.

Unfortunately, unless there are updated 64-bit drivers for the application you’re trying to run, you’ll have to disable driver signature enforcement. Consequently, your system will be more vulnerable, so it depends on just how desperate you are for the application.

Disable Driver Signature Enforcement

We can use the advanced boot options menu to boot Windows 10 with driver signature enforcement disabled. This is not a permanent change. Driver signature enforcement will be enabled next time you restart Windows 10. However, your drivers shouldn’t be removed.

Open the advanced boot menu by pressing Shift while you click Restart.

windows 10 advanced boot options troubleshoot

Select Troubleshoot > Advanced Options > Startup Settings. You should have arrived at this screen:

windows 10 advanced boot options startup settings

Press Restart.

windows 10 startup settings restart

Type 7 at the Startup Settings screen. This activates the “Disable driver signature enforcement” option. Press Enter to boot your system. You’re now free to install unsigned drivers!

4. Virtual Machines

Windows 7 included a “Windows XP Mode.” It was an excellent feature that was essentially just a virtual machine with an XP license. Nonetheless, it made booting older applications that bit easier. Unfortunately, Windows 10 doesn’t have an XP mode. However, we can use a virtual machine to create our own XP mode.

create virtual machine for windows xp in virtualbox

All you need is a virtual machine, like VirtualBox or VMware Player, and an old — but crucially, spare — Windows XP license. Install your Windows XP license in the virtual machine, and you’ll be able to run your application in the older version of Windows, in a window on your desktop.

Realistically speaking, this isn’t an ideal solution. As well as this, the success of a virtual machine depends on the application. Virtual machines have limited hardware support.

5. DOSBox

If you’ve got an old DOS program or game refusing to work, DOSBox is going to be your friend. DOSBox is a free application that runs a full DOS environment on your Windows 10 system, allowing you to run old DOS games and applications.

windows 10 dosbox old program

DOSBox brings hundreds of classic games back to life. It is extremely well used, meaning if you’re stuck, there will be a solution online. Similarly, you can purchase games via GOG.com pre-packaged to run in a DOSBox instance.

Old Is Gold

Nostalgia is a powerful attraction. I know: I love booting up old games 10+ Emulators To Play Old-School 16- And 32-bit Consoles On Your PC (1987-1993) 10+ Emulators To Play Old-School 16- And 32-bit Consoles On Your PC (1987-1993) Read More . Windows 10 doesn’t always want to play ball, though. Ideally, you’ll be able to find modern alternatives for old applications. However, it isn’t always possible, and just isn’t possible for some business applications.

Luckily, one of the methods we’ve detailed above will be the solution, so give them a try!

What old game are you firing up? Or do you have old software you depend on? Let us know what you’re up to!

Image Credit: Sunny studio via Shutterstock.com

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  1. D Witz
    August 15, 2017 at 6:56 am

    Yeah, I've never had their compatibility troubleshooter work for any game. It's like they're claiming they change something and then just use the main operating system instead. I'm trying to run Monty Python's Complete Waste of Time and so far it's living up to its name more than ever. I tried running it in Windows 95 mode, even, and not a thing changes. I dunno why they promise these things if there's a bunch of stuff needed to do it that they don't have anymore. Anyway, I may see if my husband has a spare license once he's awake. He's in IT so he has all sorts of ancient artifacts laying around...

  2. colleen
    January 20, 2017 at 1:10 am

    It seems to be just clearing the box when I hit submit

  3. colleen
    January 20, 2017 at 1:09 am

    microsoft picture it 98
    microsoft publisher I think it's 2000 version could be 98 also however. I know they have this new version on line, but it loads slow and saves where it wants and agian with poor internet reliability not an option. I like and am used to these old programs and their simplicity.