How To Run Legacy Applications in Windows XP & Windows Vista

Page content

Why Use Old Applications?

I personally have run DOS applications for point-of-sale-programs and as a front-end for databases. There are many business applications where a simple interface with minimum features works for the best, especially when running back-end operations and managing machines remotely. While many users will find DOS unattractive, clunky, and lacking in features, the very simplicity of many legacy programs are exactly what can make them the best choice for many jobs.

In addition, gamers will often wish to play older games that weren’t designed to run in a Windows environment. Often older games were written in a way that their timing was based on the speed of your processor, so they will zip around and be unplayable. Problems with sound, hardware interrupts, and other artifacts of a bygone age of computing plague some of the greatest classic games of all time, and so special solutions have to be devised.

Microsoft’s Contribution to the Effort

While many company’s labor over whole issue of backwards-compatibility, no one has had to work harder on this issue than Microsoft, with their vast market share and virtual omnipresence online. Their solutions are quick and simple, but don’t always work, and mostly apply to 16-bit applications intended for Windows 95 and 98.

  1. In both XP and Vista, right click on the executable of the application you wish to run.
  2. Select “Properties”.
  3. Select the “Compatibility” tab on the “Properties” dialogue box.
  4. There will be a number of options. Choose “Windows 95 or 98 compatibility mode” and if that doesn’t work, experiment with the other options.

Both of these compatibility modes use a method involving limiting the kind of memory space the program uses and what kind of calls it can make to the video and audio resources in the operating system. If you need run a DOS program, these compatibility modes are not as useful, and so you need a different solution.


DOSBox is essentially an emulator, which improves its method over Microsoft’s compatibility modes. It creates an emulated environment that replicates the exact conditions of a fully loaded Intel x86 PC, and deals with all the drivers from within that environment. Their official site claims that this should work for all DOS applications, though their focus is on games.

Let the user beware: there is a downside to using DOSBox. It is not for the timid, as it will require the use of the command line to configure. This can be tricky by itself, but some games will require special tweaking via additional settings, also from the command line. DOSBox can also crash at bad times, especially since legacy programs often had no autosave features. On several of the DOS games I tried, especially some of the old interactive fiction games that included graphics and cued sounds, a crash resulted in the loss of data. Overall, however, it was stable and allowed me to enjoy some classic games.


FreeDOS is an operating system, fully compatible with MS-DOS. This is one of the best of the DOS variations, of which there are many. It is maintained, open source, and ran just about everything I threw at it. However, there are some issues involving drivers for new hardware and networking legacy applications, as one would expect, but these problems are minimal. Best of all for those of us trying to avoid the command line, it has a graphical interface!

Final Word

Running legacy applications can be a real pain, but these solutions will work for most of them. While none of them are perfect, between them I have yet to find a legacy program that, with a little tweaking, I can’t get running. The question becomes whether you are willing to do the tweaking.

Good luck!

Flock, the Social Web Browser

FireFox 3 Extensions Roundup: Social Media and Blogging

Digsby: Instant Messaging for Web 2.0

5 Firefox Extensions to Enhance Your Online Life