I plan to install Windows 3.0 and PC/GEOS on top of DOS. Plus I will install numerous games from the 1984-1992 timeframe. Some of the later games will require >640K RAM and make use of an EMM driver.

I am mainly debating between using MS-DOS v5 or FreeDOS. MS-DOS 5 is appropriate for the time period, and I know it will support the 4 MB of RAM and the 2 GB HD partition that I am planning. FreeDOS, on the other hand, is obviously much more modern and maintained. However, it is a re-engineered version of DOS and probably has compatibility issues.

To me, FreeDOS seems like the safe choice for finding help online and for being able to have all the "modern" DOS niceties. But MS-DOS 5 seems like the "safer" choice for compatibility with the applications and games I want to install.

Which DOS would be the better choice, OR is there a third option I should consider above either?

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    You may want to weight in licensing too: AFAIK, MS-DOS is (still) not free. – Konamiman Apr 17 '17 at 6:50
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    Also, in 1990 the Amiga was still the king of the gaming rigs for at least a couple more years. PC games tended to be ported from other platforms, and were often inferior versions of the originals. So if your interest is retro-gaming, a purist might argue you ought to either jump forward a couple of years, or pick a different platform. – T.E.D. Apr 17 '17 at 18:03
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    In addition to what T.E.D. said, many PC games released in the time frame you're looking at would have speed issues on a '386. In 1990 a '386 PC was very expensive, very few people would have one at home. Especially for pre-1990 games, if you want to stick with a PC instead going with a more era appropriate platform, I'd recommend getting an 8088-based PC, like a Turbo XT. This is the sort of PC people would have been gaming on. CPU speed is the biggest compatibility issue for MS-DOS games and a '386 is only at the right speed for games released in 1992-1994 or so. – user722 Apr 17 '17 at 18:46
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    retrocomputing.stackexchange.com/q/1352/79 might be relevant. If you want to experience the full range of PC games (booters and DOS games) you need a number of PCs: a toggleable 4.77MHz/8MHz 8086 for the oldest games, a 33MHz 386 for many eighties and nineties games, a Pentium for mid-nineties games, and an all-out 800MHz Pentium III for the last DOS games. There are some games calibrated for 286s or 486s but they’re rare. Mo’Slo anyone? – Stephen Kitt Apr 18 '17 at 7:19
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    @wizzwizz4 Yes, but only for v1 and v2: computerhistory.org/atchm/microsoft-ms-dos-early-source-code – Konamiman May 12 '17 at 8:44

If you’re going for strict historical accuracy, a 1990 PC could have had either MS-DOS/PC-DOS 3.3, MS-DOS/PC-DOS 4.01, or DR DOS 5, along with Windows 3.0. MS-DOS 5 was released in 1991, and DR DOS 6 followed in the same year. An interesting OEM option is Compaq’s 3.31 DOS, which included support for partitions larger than 32MiB, and the first expanded memory manager (CEMM).

Of all those options, I’d say DR DOS 6 is the most convenient: it has the most memory optimisation features of the lot (Compute Magazine, June '92 review). You could also try MS-DOS 5, perhaps with QEMM or DOSMAX if you need more conventional memory. (You’ll need a boot menu anyway because many early nineties games aren’t compatible with V86 memory extenders.) Both of these would be period-accurate for 1992.

If you’d rather go for convenience, your options widen: you could use MS-DOS 6.22, OpenDOS 7.03, or FreeDOS. All three are pretty much on a par in terms of usability: while FreeDOS has better tools, you’ll find far more information online about MS-DOS and to a lesser extent OpenDOS. (All three include good documentation of their own.)

While on the subject of convenience, I’d also recommend going for Windows 3.1 or even Windows for Workgroups 3.11: they’re not historically accurate for 1990 either but they’re much more usable than 3.0. If your reference point is 1992 then Windows 3.1 is fine.

Of course all this ignores the question of licenses. It was also common in those days to install loads of utilities to alleviate the OS’s deficiencies, which levels the playing field too.

I actually bought a PC in 1992; I got a 33MHz 386 with 8MiB of RAM (which was a lot at the time), a 120MiB hard drive, and DR DOS 6 and Windows 3.1. My only regret in the years that followed was not spending a bit more to get a 250MiB drive. I knew someone who had a gigabyte SCSI drive in 1992 but that cost half an engineer’s monthly wage (10 000 FF).

  • IBM DOS 4.01 would be historically "correct", too, although I guess by that time there weren't any significant differences between IBM DOS and MS-DOS; those started a bit later. – Jörg W Mittag Apr 17 '17 at 12:51
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    My recollection is MS-DOS 4 was not very stable or popular, and many people skipped from v3.3 to v5. I'm mostly thinking in terms of the machine being in use from 1990 to 1992 or 1993. So, by the end of its "service life", the likely upgrades would include MS-DOS 5, and Win 3.1 too. – Brian H Apr 17 '17 at 14:53
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    DOS 4.0 was quite buggy, 4.01 was OK but used lots of memory without really adding much of value compared to 3.3. Compaq had an interesting 3.31 which supported larger partitions and included an extended memory manager (CEMM). – Stephen Kitt Apr 17 '17 at 15:39
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    @BrianH There were two versions of MS-DOS 4, Microsoft's multitasking version and IBM's more or less normal version. The multitasking version was only released to a few European OEMs, while IBM's version was the one with all graphical front end and all the bugs. I wouldn't recommend using either. – user722 Apr 17 '17 at 18:14
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    @Joshua Abandonware isn't legal in the first place, though it's usually a victimless crime :) A lot of previously "abandoned" software has been recently brought back, too. That said, back in the day where I had a MS-DOS only machine, I didn't even realize that software was supposed to be sold - everyone just copied floppies, often with multiple pieces from different vendors on the same disk. I know people who still feel that's perfectly fine... – Luaan Apr 18 '17 at 8:27

I'd say it depends:

Plain old DOS is not such a complicated operating system that a free alternative like FreeDOS would really cause severe compatibility problems - At least as long as you stay within the lower 640k. FreeDos is the easiest to obtain and doesn't come with in-built licensing implications.

Himem and EMS might cause one or the other compatibility issues. But not only between free and commercial alternatives, also between the various commercial DOS vendors and versions.

I am using FreeDos with all my old PCs and have not experienced any such problems up to now, though. Support for "newer" hardware, like USB and networking, which tend to come in handy for transferring software to the legacy machine, is also much better on FreeDos than of any of the legacy systems.

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    "Plain old DOS is not such a complicated operating system" ... yes it is, since application software of that vintage had a nasty habit of having its own idea of what was API and what was OS internals. – rackandboneman Apr 19 '17 at 8:51
  • I'm not sure licensing for DOS is all that complicated. It's still pretty easy to find "un-opened" or "un-used" DOS disks in original packaging on eBay for not much money. Assuming the seller is legit, I don't see any licensing issue with installing one of those on some computer a guy builds for fun. – cbmeeks Jun 21 '17 at 20:02
  • I'd rather have "opened and TESTED" :) Also, most of the DOS media in circulation is indeed vendor OEM, which make it theoretically more complicated legally. – rackandboneman Dec 6 '17 at 16:56

I remember running a version of DOS 4.0 on my 1989-era 386sx machine, along with DesqView/386. Shortly thereafter, we installed Windows 3.0 and then MS DOS 5.0... As far as being period correct and useful, that would be a reasonable place to start. Given the expected life of that 386 box, you could go as new as MS DOS 6.22 and WfWG 3.11 and still be within the realm of possibility.

(BTW, if the goal is period correct, that's not a 2GB Disk. Even 80MB disks sold for around $500-600. I know of at least one late 80's 386 machine with a 1GB disk, but it was a large external box and the application was quite high-end.)

Edit: Corrected timeline, thanks to Michael Kjörling.

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    Wikipedia puts the release of MS-DOS 5.0 on June 11 1991. Windows 3.0, on the other hand, was released on May 22, 1990. Thus, Windows 3.0 predates MS-DOS 5.0 by over a year. MS-DOS 4.01 was released in November 1988. Windows 3.1 (April 6, 1992) would probably be period-correct with MS-DOS 5.0, though; MS-DOS 6.0 was released in March 1993. – user Apr 18 '17 at 9:15
  • I was one of the people that ran the MS DOS 5.0 / Windows 3.0 combination.... – mschaef Apr 18 '17 at 13:29
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    ...though probably not in 1990. – user Apr 18 '17 at 13:30

In late summer 1994 I upgraded my original IBM AT to DOS 6.22. I had the OS on a 20mb drive and games on a 40mb drive. It was using an Intel AboveBoard with 2 mb memory which I had been using since DOS 5. It was using an enhanced 32kb EGA video card. I do not recall having any difficulty with any of the installed games.

My first Packard Bell Pentium 75 came with DOS 6.22 and Windows 3.1 for workgroups on it. That ran some of my old games too fast.

I currently have an IBM Thinkpad 360c which is a 486 DX 50 that runs my old games. It has DOS 6.22 and Win3.1 for workgroups.

I have never tried FreeDOS on any machine that old. I do use it on an old Athlon II but some games just don't run correctly. Any game with a PCI or AGP graphics incompatibily will have issues. Not many do.


  • I use DOS6.22 because it has interlnk. Sometimes that is the only way of getting stuff across to an old pc unless you wish to play with ethernet. – cup May 16 '20 at 4:39

I've used DOSBox for the exact same purpose, i.e., playing old games. I found it to be much easier to configure for various things (Soundcards, EMM, Ramdisks, etc.) which many games of old needed. Best of all you can run it on current hardware so you won't have to dig up an old vga monitor out of a landfill.

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    Good point. Lots of people prefer emulation. But I have lots of old hardware and that is more my area of interest than the games, per se. – Brian H Apr 17 '17 at 14:58
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    In my experience, lots of games are much more enjoyable on real hardware than on DOSBox; anything involving action of some sort is particularly sensitive to the latency and variability you get with DOSBox. Other, more accurate emulators such as PCem provide a better experience, especially for older hardware, but it’s still not quite the same. Also, many LCDs work fine with older display adapters (as long as it’s VGA or later). – Stephen Kitt Apr 17 '17 at 16:00
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    Emulators have their place but there is nothing like playing on real metal. Also, DOSBox doesn't emulate those loud PC fans keeping that 386SX monster cool. ;-) – cbmeeks Apr 17 '17 at 19:20
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    @cbmeeks Fans? My 486DX was 100% passive cooled. The only noise I had was from the hard drives and floppies - and later, the CD drive (incidentally, I've used an AtariST emulator that emulates the floppy sound as well for extra nostalgy :P) Most of the 386's and 486's I've seen or had were either passive or with just a tiny-winy fan. – Luaan Apr 18 '17 at 8:23
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    The power supply fans were very loud back then, these were the days before there was any on-demand control of fan speeds. 386, 486 and even some very early pentium (pre-MMX, true i586 not i686+ type!) systems were indeed often not equipped with fans or even heatsinks on the CPUs; fan-assisted CPU coolers were introduced into general PC technology with the 50MHz version of the 486DX (the original 50MHz FSB type, not the later DX2/DX4 styles that ran a lower FSB!). – rackandboneman Apr 20 '17 at 9:12

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