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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.

  1. Chris
    October 17, 2016 at 3:25 am

    I'm trying to get virtual turntables carrot innovations running on a newer operating system. I'm in a band that has been using this software since it came out. It's very important for us since its features all in one program is impossible to find. I have access to Linux but not all the feature work. I'm running Ubuntu zorin 10. Any ideas or any suggested distributions would be greatly appreciated. Thanks for your time.

  2. Nancy
    September 13, 2016 at 5:54 am

    I found this article when searching for ways to run Mazemakr (from Custom Real-Time Software) which was written for Windows 3.1 in 1992. I found an emulated version on archive.org which is how I figured out it was Win3 and therefore 16-bit. I think I'll give one of your methods a try when I need to avoid real work. :-)

  3. Michael Gene Muldoon
    July 7, 2016 at 6:14 pm

    I use Lotus 123 Version 5 quite a bit at work. There is a ticket printing spreadsheet I use a lot for our asphalt plants. I can't even update to say Millenium Edition because 5 has database capabilities they removed from their later versions. So it's old even by Lotus standards. And Lotus was killed by IBM even though they use the name Lotus Symphony is NOT the old Lotus. It is just a rebranded OpenOffice clone. So.... my sites run old 32 bit machines with XP because that's what my spreadsheet needs. All of the new work machines in my company are 64 bit so they won't run Lotus at all because there never was a 64 bit version that I can find. I do have it running if you it that by running a Windows 7 virtual machine inside Windows 10 then running a XPMode machine in there then running Lotus in that. I may be driving my computer into a nervous breakdown but it WORKS!

    • Kelsey Tidwell
      July 8, 2016 at 1:23 am

      I remember tinkering with the old Lotus 123 at my dad's place of employment when I would occassionally visit there as a kid. Green screens. Somehow, thinking about it, all I can hear are symphonies of dot-matrix printers...

  4. Dave Wise
    June 24, 2016 at 11:04 pm

    I just used Virtual XP Mode to run a Turbo-C program I wrote in 2001 to edit paper tapes for a computer made in 1960. Of course I called the editor TECO.

  5. عبدالرحمن الشياب
    May 30, 2016 at 1:18 pm

    QBASIC

    • Kelsey Tidwell
      July 8, 2016 at 1:19 am

      That's a blast from the past :)

      As a kid-geek I wrote a QBASIC program to simulate model rocket trajectories so I could design my projects faster without destroying property (or my grandfather's cows).

      Thanks, Abdul!

      • عبدالرحمن الشياب
        July 8, 2016 at 8:01 pm

        You are welcome?

  6. Glenn
    April 24, 2016 at 3:06 am

    I write MUSIC and I still love the WINCAKE interface over the Cakewalk Pro Audio. I can run it using VMWARE but I wish there was a simpler "Shell" to put it into.

  7. Will
    March 18, 2016 at 11:44 am

    I run a Windows 3.11 VM in virtualbox and have Windows 3.11 running in Boxer on my Mac, for all my 16 bit windows gaming.

    Only difficulty I have is MS Golf, seems to crash on Dosbox and be too fast to click in Virtualbox.

    • Justin Pot
      March 22, 2016 at 1:37 pm

      Emulation is rarely quite perfect, but tweak things a bit and you can get close, seems like you've learned a lot already.

  8. Ken Holland
    March 15, 2016 at 4:42 am

    I've got a laptop that run XP and came across some of my old files from the DOS/Window 3.11 days. I haven't gone through it all very thoroughly but there are some games and Borland C++ Version 7.2. Also I found MS C++ (This one may be just straight 'C') and MASM Version unknown at this time. I think there may be source code for some of the games. I just have to do more looking at the files.

    Ken

    • Justin Pot
      March 15, 2016 at 10:57 pm

      Let us know about anything else you find!

  9. jeep
    February 6, 2016 at 8:08 am

    virtual pc works also

  10. Robert Bailey
    September 18, 2015 at 9:28 pm

    Hello, I'm trying to run Autosketch release 2 on a vista machine. I only have 3.5"disc. Any advise on how to run?

  11. Nathan Hardwick
    August 9, 2015 at 8:19 pm

    I am running a National Geographic Digital Collection from 1996, designed for 3.1 and 95.

    • Justin Pot
      August 10, 2015 at 12:25 am

      That's amazing, is it just an archive of all the back issues? How do the images look on modern computers?

      • Nathan Hardwick
        August 10, 2015 at 2:18 am

        It is a digital scan of all of their magazines from 1888 to 1996. The quality is okay, really, since the text is readable but the pictures are not full quality. I picked it up at a local library sale.

    • Justin Pot
      August 10, 2015 at 4:08 pm

      That's pretty cool, I bet there's a lot worth reading in there. Glad you got it working.

      • Nathan Hardwick
        August 10, 2015 at 5:42 pm

        Thank you for the tips!

  12. Rob
    May 2, 2015 at 5:23 pm

    I am still using (16 bit) Sidekick 98 for my work, but now I have problems getting it to run/unzip from my CD to the virtual XP mode in a 64 bit Windows 7 Pro laptop. When I try to run it, the DOS screen comes up for a second and disappears.

  13. Mike G
    April 27, 2015 at 6:27 pm

    Absolutely. And speaking of MS-DOS, Lotus123R5 came out in two versions - one for DOS, and one for Windows 3.1., which itself ran under DOS as I understand it. So I *should* in principle be able to run Lotus123R5 for Windows under a DOS emulator! I get the impression though that DOSBox and similar emulators are 'good enough' (or maybe even 'pretty good'?) emulators, but don't have the *full* functionality of real DOS. I do a google browse to check this out once a year or so - I think the time has come again ....

    • Justin Pot
      April 27, 2015 at 6:29 pm

      DOSBox is a pretty competent emulator, but it's built with games in mind. Things like printing are basically impossible, but it does run software exceptionally well. Best of luck to you keeping everything working.

    • Doc
      May 3, 2015 at 2:09 am

      If you can find (legally) the floppies for it, you can run Windows 3.1x in DOSBox, and load generic display drivers, etc. to get 256+ colors and sound as well. http://www.vogons.org/ is a great resource for everything you'll need except the copy of Windows itself.

  14. Mike G
    April 27, 2015 at 5:53 pm

    I use it for almost everything that involves (or can benefit from) computation, analysis, sorting etc such as: 1. time recording - I used to work in professional practice where time was charged by the hour and I developed, incrementally*, my own real-time software which I still use - it really 'holds up the mirror' to just how easy it is to fritter time away on unplanned 'stuff' 2. accounting - my small-business accounting (customised to MY needs) 3. To-do listing, planning, scheduling etc. In fact the only area where I don't use is for text-based notes, webpage extracts etc, for which I use ActionOutline.

    *one point I didn't mention is that Lotus123R5 lends itself to a 'kaizen' style of development: small, incremental improvements to code as and when a possibility of improvement is noted.

    I rarely have to export files to others: when I do, I can save-as in .xls format from Lotus123.

    • Justin Pot
      April 27, 2015 at 6:05 pm

      Thanks for taking the time to answer that, fascinating stuff. I've been really interested in people using decades old software ever since I learned that George R.R. Martin still uses an MS DOS word processor to write his novels.

      Sometimes, if a tool is familiar to you, it's the best tool for the job – period.

  15. Mike G
    April 26, 2015 at 2:21 pm

    "Is there any 16-bit software you’re still using for actual work? "

    Yes. All my spreadsheet work is on Lotus 123 Release 5 for Windows, which has a powerful keystoke-macro programming language.

    I'm aware that Excel has a 'keystroke capture' facility to turn keystrokes into macro commands. That though is a poor substitute for the 'flow state' that arises from programming 'immediately as you think' - in much the same way, perhaps, as an author who writes longhand finds his creativity 'bottlenecked' by the slow capture mode of handwriting, as compared with using voice-recognition software.

    Part of the power of the Lotus keystroke macro programming is that it is relatively simple to program for the macro to edit itself as it runs, where that is more straightforward than using a byzantine structure of IF..THEN and BRANCH statements for the matter in hand.

    • Justin Pot
      April 27, 2015 at 5:13 pm

      This is fascinating ,and I'm really curious: what kinds of things do you use this spreadsheet software for? Is it for your job? Do you have trouble collaborating with people because of your (relatively) obscure preference?

  16. snaid
    March 31, 2015 at 2:31 pm

    old games, specificallt
    Castle of the winds

    • Justin Pot
      March 31, 2015 at 2:41 pm

      I've never heard of this one! Look interesting.

    • Doc
      May 3, 2015 at 2:07 am

      Castle of the Winds (shareware and Castle of the Winds II, paid) was a wonderful RPG (tile-based graphics) designed for Windows 3.1x, although in order to use the numeric pad for movement, you had to turn Num Lock OFF. Either game came on one floppy, and ran fine in Win 95 & 98, and (IIRC) XP and Vista 32, as 16-bit program support didn't disappear until 64-bit came along.

  17. Sam Datum
    March 9, 2015 at 11:22 pm

    Here's one for you. I used the program below, sporadically, until we changed to 64-bit Win 7 machines at work. I have another company-purchased statistics program (>$1200, 130 MB Install) but I like MSTAT because of it's specificity. Now I understand I'll need to either emulate or simulate a 32-bit windows environment to make it operational once again.

    MSTAT or MSTAT-C is a statistical design and analysis software written by Dr. Russell Freed at Michigan State University. First released in the 1980s it has been used by the researchers in the fields of plant breeding and life science across the world (MSTATC was released in 1990s). It almost certainly is still widely used, particularly in Third-World countries where resources are limited. Not bad for a 1.5MB application that fit on a floppy. I believe it's still available. https://www.msu.edu/~freed/mstatc.htm.

  18. Doug Taylor
    March 5, 2015 at 9:34 pm

    Actually, yes, I use a very small and fast calendar/note/timekeeping system I wrote back in 1991 currently in WIndows 7 OS. The program is a small 35K .com file,extremely fast to load and shut down, and does all I need to do, copy and paste below in notepad to see character version of this app,

    ????????F1=Help???????????03/05/2015?????????????(c) Cymbolic Systems 1989-1997?
    [3.5]code Review   ?
    ??????<??=Edit Day??????[2]Tri-County Req Change to Intern Extract   ?
    [2]backups   ?
    ????????F1=Help????????? ?
    ?
    ? 8 9 10 11 12 13 14 ? ?
    ? 15 16 17 18 19 20 21 ? ?
    ? 22 23 24 25 26 27 28 ? ?
    ? 29 30 31 ? ?
    ? ? ?
    ???????03/05/2015??????? ?
    ?Plnt Source code: ? ?
    ?cymbolic@yahoo.com/jaz? ?
    ?zyy22  ? ?
    ?  ? ?
    ?   ? ?
    ?   ? ?
    ?   ? ?
    ? ? ?
    ? ? ?
    ? ? ?
    ??To Do???????????????????Now: Thursday, March 05, 2015??????????????15:33:04???

    • Justin Pot
      March 5, 2015 at 9:46 pm

      I think we're not seeing a lot of the code here, but this is still really cool. Thanks for sharing!

  19. Dennis
    August 30, 2014 at 6:05 pm

    Also you can use the free VirtualBox to run Win95 or Win98. Win2000.
    I even had the old Windows NT running with VirtualBox.
    It's fantastic for operation system virtualization.
    So there shouldn't be a big problem running old games.

    • Justin P
      August 31, 2014 at 10:03 pm

      VirtualBox is a solid option, especially if you still have your Windows CDs lying around. Just remember: it's probably a good idea to turn networking off for these systems. Virtual machines can get viruses same as any other, and operating systems that haven't seen updates in a decade aren't going to be easy to protect.

    • Doc
      May 3, 2015 at 2:02 am

      I haven't heard of anybody getting Win98 working in DosBox (at least without a lot of tweaking), although I easily got Win95 working. Windows 2000, as it runs an NT kernel, will likely never work in DosBox, but should work fine in almost any other virtualization program (VirtualBox, Bochs, etc.)

  20. Dennis
    August 30, 2014 at 5:59 pm

    --> Commander Keen
    On the Mac playable with the free Boxer.app
    Even in full screen.
    This app comes with Keen and Pinball
    --> http://boxerapp.com/

  21. Floyd
    August 24, 2014 at 8:41 pm

    I use QDEX (search for qdex122f) which is a wonderful little card-file program from way, way back. With Win7 Home I set up a WinXP VM with Virtual Box. A bit clumsy so on my laptop (WIn7 Pro) I used the WinXp extensions and it works well. Very simple program, card file loads into RAM and is really fast to search. It is a free-form database, but text only. Evernote and One Note are far more sophisticated but this excels with its simplicity and speed.

    • Justin Pot
      August 25, 2014 at 12:19 am

      Glad you got this working, I'll have to look into this ancient program. I wonder what other productivity tools from the past people are still using...

  22. Jared
    August 23, 2014 at 12:07 am

    I had to set up a virtual machine on in order to run Floor Plan Plus 3d, and old old old piece of building design software for a construction business. I tried setting up a portable app, but still wouldn't work with 16 bit software.

    • Justin Pot
      August 25, 2014 at 12:18 am

      Yep, making something portable sadly makes no difference. If only WINE could run in Windows, then we could get something cooking...

  23. g.m.nelson
    August 22, 2014 at 4:56 pm

    I run Calendar Creator Plus 5.0 in DosBox on a Vista 32bit system, it will run directly but with the wrong keyboard (my laptop has a spanish keyboard) while in DosBox it sees the proper keys. I have not been able to find a modern calendar program that lets you store events/birthdays etc and print a weekly/monthly calendar using the stored database.

    • Justin Pot
      August 22, 2014 at 5:56 pm

      That's fascinating. Apparently George RR Martin writer Game Of Thrones in an old DOS word processor, so you're not alone on finding a tool that told to be the best thing for a specific job.

  24. Chad
    August 22, 2014 at 2:42 pm

    Montezuma's Revenge - that game is so hard (harder now that I'm older), but I still love it!

    • Justin Pot
      August 22, 2014 at 5:55 pm

      Have you gotten it working?

  25. Doc
    August 21, 2014 at 10:12 pm

    One 16-bit game (for Windows 3.1 with Win32S and Windows 95 and 98) that I'd like to get running again (without crashing!) is Deadlock: Planetary Conquest. Unfortunately, it doesn't seem to like Windows XP or Windows 95 in DosBox (yes, it's possible to run Windows 95 from a VHD file in DosBox!)

    • Justin Pot
      August 22, 2014 at 5:55 pm

      If you want a shortcut, GOG.com offers a version of this game that should run for you without any problems:

      http://www.gog.com/game/deadlock_planetary_conquest

      But failing that, have you considered trying a virtual machine instead of DosBOX? It's an easier thing to do than installing 95 in DosBOX (seriously impressed by that, by the way...)

    • Doc
      August 24, 2014 at 11:59 pm

      Tried installing it on Microsoft Virtual PC running Windows XP; no go. Will have to try MSVPC + Windows 98SE combination...that might just work!

      PS: Why is it when I go to the MUO homepage, I'm logged in, but on many other pages I'm not? Weird...

    • Justin Pot
      August 25, 2014 at 12:17 am

      I've no idea what's up with login, but it's unique to this article. I've had to manually add my email address to every comment I make on it, and I'm the managing editor of this site. : Luckily, we're replacing this third-party login system with one of our own next month.

    • Al
      February 26, 2015 at 12:58 pm

      I'm trying to run an old data type program "Professional File 2.0" on my Windows 8.1 machine. Wishful thinking??

    • Justin Pot
      February 26, 2015 at 2:36 pm

      Al,

      If it's DOS program, you can probably get it to work in DOSbox (but printing anything pretty much ever is out of the question).

    • Doc
      February 27, 2015 at 1:12 am

      @Al: Nope, as I stated it required a minimum of Windows 3.x with the Win32S (Windows 32-bit) extensions (the sample program Microsoft supplied with it was the first Windows FreeCell!)
      Deadlock ran perfectly fine in Windows 95/98/98SE (never tried Millenium). The biggest problem with getting it running under XP was sound; the version of Miles Sound System for Windows it used was horribly buggy; even Vogons http://www.vogons.org/ had problems with it, and could never get it stable...

    • Leona
      May 2, 2015 at 11:59 am

      Okay here goes
      first of all let me give you back your years of life... if your game is not 2d or 8 bit forget dos box it won't work and virtual box is a pain in the bum and compatibility mode is a joke. Go to Microsoft and download windows xp mode virtual pc.

      If you are trying to play a windows 95 game on windows xp mode virtual provided by Microsoft do this...

      Launch your xp mode windows virtual of window
      Go to tools tab
      Ensure your option - enable integration features is on (check settings underneath that option and go to 'integration features' and make sure that drives is selected with every box in it.)
      Put in your cd
      Go to my computer
      Look down under your normal 'devices with removable storage' - you should see 'other' and in there drives like c, d and e might also say on 'yourname' - PC.
      Go to D and double click.
      There you should see your CD-ROM icons exactly as they should look. Find programme and double click and it should work.

      likewise if this doesn't work
      go back to enable integration features and make sure this is disabled, it will make the 'other' dissapear but should allow you to run the game in d drive as normal and I mean the d drive still within the xp mode window.

    • Doc
      May 3, 2015 at 2:00 am

      @Leona: Tried almost all of these, I'm on Windows 7 and will be upgrading to Win10 a few months after it comes out (retail).
      Deadlock won't run under Windows XP (or XP Mode) with sound enabled, and Vogons ( http://www.vogons.org/ ) knows all the ins and outs of getting old games running under new OSes, so "Virutal XP Mode" won't work.
      I have managed to get it running under Windows 95 running in DosBox (getting that set up and working is another challenge in and of itself, but is a worthwhile and fun challenge). It's just a hassle, as Deadlock doesn't like any screen resolution higher than 1024x768.
      Also, I don't recommend running XP (or XP Mode) as both are currently unsupported with no new security patches being released (and XP Mode, as a virtual machine, requires its own antivirus and security updates)

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