How to Run Old Games and Software on Windows 10

Gavin Phillips Updated 14-12-2019

Microsoft tries to make programs and file formats backward compatible. It doesn’t always work. Sometimes the gap between operating systems is too far and your favorite old Windows game 10 Old PC Games Still Worth Playing Today Playing old PC games can fill you with nostalgia. Here's our list of the best old PC games you should still play today. Read More or software will fail to work.


Applications designed for Windows XP, Windows 98, and older are now starting to struggle. Many cease to function unless you find a specific Windows 10 fix for the older software. Even using the Windows 10 built-in compatibility modes, some programs refuse to come back to life.

Before you give up hope, try these tips to get your old Windows games and programs running on Windows 10.

Why Don’t Old Games and Apps Run on Windows 10?

Some old games and programs do run on Windows 10. It depends on the program. If the program or game is especially valuable to its user base, a workaround might exist. Otherwise, you should consult this short list of reasons your old software is refusing to play ball with Windows 10.

How to Use Old Games and Programs on Windows 10

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. Developers coded applications with the assumption they had administrator access and will fail if not.

red alert run as administrator


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


Select Advanced > Run as Administrator, then Next to proceed.

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 the greatest football management games ever made: Premier Manager 98.


Select Try recommended settings.

run program use recommended settings


Once you apply the settings, 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

Program Compatibility Failure

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

3. Manual Compatibility Settings in Windows 10

You don’t have to use the troubleshooter to figure out how to play old games on Windows 10. You can access Windows 10 compatibility options through the application Properties menu.

premier manager 98 properties option

Select the Compatibility tab. Use the Compatibility mode option to run your application in a previous version How to Run Really Old Software on a 64-Bit PC: 6 Methods Windows reverse compatibility is fading with every advance. Here's how you can run 16-bit programs on your 64-bit Windows. Read More 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 > 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.

4. Unsigned Drivers

64 and 32-bit Windows 10 uses driver signature enforcement. Driver signature enforcement requires all drivers to have a valid signature. Driver signing helps with security and stability, ensuring malicious or unstable drivers don’t slip through the net.

In some cases, your old game or program will not use up-to-date drivers. In that instance, Windows won’t let the program install or run. However, you can disable driver signature enforcement—but your system will become slightly more vulnerable afterward. It all depends on how desperate you are to play the game or use the program.

Disable Driver Signature Enforcement

You can use the Advanced Boot Options menu to boot Windows 10 with driver signature enforcement disabled. Using the boot option to disable the driver signature signing is not a permanent change, and the enforcement will reenable next time you restart Windows 10. However, it should remove the drivers you install while the enforcement is switched off.

Open the advanced boot menu How to Factory Reset Windows 10 or Use System Restore Learn how System Restore and Factory Reset can help you survive any Windows 10 disasters and recover your system. Read More 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

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

5. Use a Virtual Machine

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, you can use a virtual machine to create your 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. The success of a virtual machine depends on the application. Furthermore, virtual machines have limited hardware support.

6. 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 How to Play Retro Games on Any Platform With DOSBox Want to play retro PC games on your computer, phone, or game console? Here's everything you need to know to get started with DOSBox, including the best games to emulate! Read More .

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 pre-packaged to run in a DOSBox instance.

Download: DOSBox for Windows

Run Your Old PC Games and Software at Last!

Nostalgia is a powerful attraction. I know: I love booting up old Windows games. 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!

If you feel the need to play some old PC games, check out these sites where you can download old games for free 5 Sites Where You Can Download Old PC Games for Free Want to try downloading some old PC games for free? Here are the sites where you can find the best games of old, free to download. Read More  or these ways to play retro games on your PC legally How to Play Retro Games on Your PC, Legally! If you want to play retro games on your PC, this article is for you. These methods are all entirely legal! Read More .

Related topics: Drivers, MS-DOS, Retro Gaming, Windows 10, Windows XP.

Affiliate Disclosure: By buying the products we recommend, you help keep the site alive. Read more.

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  1. Ryan
    March 25, 2020 at 12:00 am


  2. tazmo8448
    January 22, 2020 at 3:56 am

    Years ago there was an Nvidia program that made older games run even if you had an AMD system (GPU) for the life of me can not remember its name. Not to be confused with graphic card drivers but a program that was built to play certain games and sometimes you had to uninstall that and replace it with a new 'legacy' version that had older .dll's and what not to make games run. Did it many times. Wish I could remember the name of it but it was made by Nvidia for game developers.

  3. Anthony
    October 26, 2019 at 10:25 am

    Hey, great article! I wanted to ask a question based on the Premier Manager series. I have PM97 (stupidly good game) and I've just bought a Lenovo Idea Centre (windows 10). I have applied all the options you have said and it wont allow me to install the game, although I have the disc and can select the PM97 anyway. When I do I get the same message,'THE GAME CANT BE STARTED, you need at least 3mb of space for game to run'. Now, on old games I found it strange that it would occasionally work and then sometimes now. I've often changed settings in the properties myself but have so far had no joy. Any ideas? thanks

  4. Ron
    July 2, 2019 at 1:48 am

    Anyone had success installing/running Microsoft Flight Simulator, 2006 xp version? We're there other steps or tricks to make it compatible beyond what was covered in the article?

  5. Ron
    July 2, 2019 at 1:44 am

    I'm trying to install and run 2006 Windows XP Microsoft Flight Simulator on Windows 10 machine. I've read this article and see many steps that may or may not work in the end. If anyone else has tried, hopefully with success, running Microsoft Flight Simulator (not the newer X version), I'd like know know if you were successful, and whether you had to do something besides what the article covered. Many thanks in advance to a kind soul.

  6. Tony
    April 27, 2019 at 2:31 am

    The problem with PM98 is it doesn't allow you to save the game. You gotta keep it running live to continue a long save. Anyone know how to get around this?

    • Gavin Phillips
      April 30, 2019 at 4:22 pm

      I run it in a virtual machine and save the entire machine state in place using the save game feature ;)

  7. Alby
    March 7, 2019 at 11:18 pm

    Mame....simply an easy to play arcade games...

    • Gavin Phillips
      April 30, 2019 at 4:23 pm

      I have a MAME emu on my phone, great for journeys!

  8. Paul
    March 4, 2019 at 3:43 pm

    Thank you Christian! My HDD activity has reduced from 100% active pretty much consistently to around 5% active, with occasional peaks when I open new web pages or apps. And the difference in noise in a huge blessing too!
    I disabled Windows Search, superfetch and turned off Flash in Chrome

  9. PS
    March 4, 2019 at 9:27 am

    Some games respond fine with compatibility mode in Windows 10 but a few refuse no matter what you do.

    My favourites that I can no longer run are Sim City 2000 (windows version) and Sim Golf. A great pity.

    • Gavin Phillips
      March 6, 2019 at 9:55 am

      You can play Sim City 2K on Classic Reload :) Sim Golf is a little harder to come by. There is a new Sim Golf style game on Steam, I think it just hit Early Access, so could be worth keeping an eye on!

  10. Donna
    February 2, 2019 at 11:25 pm

    Sigh, I found my Original Sims PC game disk. I thought wow! I haven't played this in years! I fed it into my computer and the game installed right away. But that was were it ended. The game just will not boot up. Absolutely nothing happens :-( So disappointed.

  11. Danielle
    September 12, 2018 at 4:07 pm

    I have an issue with The Great Chocolate Chase. It ran fine on every version of Windows until 10. Now it will run, but the cursor with have a square around it, or a trail of itself. Then the screen will blip periodically until the game freezes. I usually end up having to restart my laptop as the game window refuses to close.

    No compatibility mode seems to work. All the other games I have purchased from bigfish work fine. I have tried getting the game from elsewhere. Zyolm had a workable version for a time, but that went bang in the next windows update.

    I have tried where I purchased the game from -bigfish games - who were completely unhelpful. Same with Microsoft.

    If you could provide a solution, please.

  12. May
    September 8, 2018 at 2:56 am

    Hello! I have downloaded Madelines European Adventures from on my HP Windows 10. I at first got a "Wing32.dll is missing" error at first but I fixed that but now when I click on the game it says "Madelines European Adventures has not yet been installed! Please run setup.exe in the CDROM" However when I click on the setup.exe It says "this app cant run on your pc" I really want to play this game. what do I do??

  13. Quill
    July 26, 2018 at 6:42 pm

    Worked for me! Thank you very much!

  14. Rob
    February 25, 2018 at 4:42 am

    I could use some direction on running Cyberdream's 'Dark Seed II' on Win10. I once tested it successfully on an XP machine with at least SP2. I'm following the 'Properties' options shown in the above tutorial, and I'm making the various tweaks, but clicking on 'Test the program...' just never activates a pop-up. I have this game saved in several ways, including as a disc image file. DOSBox works well running all my other old games; but I haven't the experience running 'virtual drives' and don't wish to risk screwing up my true C: drive. I thank anyone in advance for providing a list of straightforward steps that worked specifically for 'Dark Seed II' on the Win10 platform.

  15. Gaz
    January 18, 2018 at 5:33 pm

    Iam trying to get championship manager 3 to work on windows 10 but I've lost touch with pcs over the last few years if anyone can help that would be great I might even have a spare copy for them if they want if anyone can help please help

  16. Wes
    December 17, 2017 at 8:14 pm

    Trying to revive Ultima IX Ascension. The above walk-through was a no-go, too bad how progress in technology seems to be more along the lines of censorship.

  17. Tolo
    December 1, 2017 at 7:15 pm

    I'm trying to play Heroes of Might & Magic IV. troubleshooter hasn't helped. driver signature didn't work. no spare license. any other ideas?

    September 29, 2017 at 6:07 am

    i cant play SEAL OF EVIL game even after doing this...PLEASE one of my best childhood games


  19. Michael Gillespie
    September 18, 2017 at 8:15 pm

    All of the above fixes won't let me play MechWarrior 3 on my Win 10. Been dying to play through the series for months.

  20. Virginia Borders
    August 25, 2017 at 3:48 pm

    Adobe Pagemaker: For years I worked in a Print Shop, using a Mac and Pagemaker. Grew to love Pagemaker and now can't find anything that is so easy to use. Word is the closest but it won't open many files that I have on my external hard drive that are in Pagemaker. Adobe is now offering InDesign for Windows 10. Has anyone used that program and is it compatible with opening up files made in Pagemaker?

  21. 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...

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

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

  23. 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.