Installing Windows 3.1 on DR DOS 6.0

I recently installed DR DOS 6.0 in a virtual machine for fun. I’d never used it before (or if I did, I can’t remember), and it was a great way to use something novel but familar when dealing with the brain fog and fatigue of a flu relapse! I was up to speed faster than I thought I would be, thanks in part to Digital Research’s excellent documentation. I should write a post about that.

Now with a functional DR DOS 6.0 environment, I wondered what the next step would be. Obviously my beloved Brown Bag Software PowerMenu and Digital Research GEM would be great, but Windows 3.1 (specifically the later Workgroups flavour) seemed like the Final Boss. Microsoft’s infamous AARD code would generate an obtuse error on early 3.1 beta installers when run on DR DOS, so it seemed fitting to name this VM AARDvark. Thank you.

Attempt 1

Let’s attach the first Windows 3.11 disk and run A:\SETUP.EXE. Will we get a functional installer?

Well, aren’t we off to a great start! I think the last time I saw that error was back in 2015-ish, when I was messing with some old versions of QEMM386 I’d bought from someone. I’d never seen the error prior, presumably because I grew up on MS-DOS 6.0 [sic].

It’s worth pointing out DR DOS handles EMS, XMS, and the high memory area differently from MS-DOS. 286 and earlier machines can invoke HIDOS.SYS in their CONFIG.SYS, similar to HIMEM.SYS on MS-DOS:

DEVICE=C:\DRDOS\HIDOS.SYS

For 386 and later machines, you only need to load EMM386.SYS, similar to EMM386.EXE on MS-DOS:

HIDOS=ON DEVICE=C:\DRDOS\EMM386.SYS

Evidently Windows didn’t like this, so I commented these lines out and rebooted.

Attempt 2

Okay, let’s try again. A:\SETUP.EXE:

That looked better! I could proceed with the installer as normal, though I soon got an error that I was running with an EGA card instead of VGA, which it doesn’t support. This was unrelated to DR DOS, so I fixed this and restarted.

The first two disks copied over just fine. But when it prepared to enter the GUI part of the installer, we got some fireworks:

It references an error running in Standard Mode, so I thought it might still be an extended memory error. I noticed the setup program loaded an “XMS memory manager” when first starting, which might not play with DR DOS. Maybe if I could get DR DOS’s EMM386.SYS working, we’d be off to the races.

Attempt 3

I wondered if the shockingly good DOSBook reference manual had any information about Windows. It was easy enough to invoke:

C:\>HELP windows

It returned this in its index:

Windows /WINSTD option EMM386.SYS

Interesting! I looked up and:

DR DOS 6.0 came out in 1991, which predates Windows 3.1x. But is Windows 3.0 similar enough? I updated my CONFIG.SYS:

DEVICE=C:\DRDOS\EMM386.SYS /WINSTD

Then I ran SETUP.EXE again. Alas, though perhaps unsurprisingly, I was back at Attempt 1 with an incompatible XMS implementation.

Attempt 4

Now, if I were living in 1991, I would have called the provided DR support number, or logged into a BBS to see if anyone else had the same issue. Doing either would have likely landed me on this same file provided by Novell Desktop Systems in 1992: The DR DOS 6.0 Update for Windows 3.1. Thank you, Internet Archive!

According to the supplied README.1ST file:

The files and information enclosed in this Windows 3.1 update contain enhancements for your DR DOS 6.0 operating system specifically and only in the area of Windows 3.1 compatibility. These enhancements include:

• Full support for Windows 3.1.

• The DR DOS EMM386.SYS memory manager now supports upper memory while running Windows 3.1 in Standard and Enhanced Mode.

Nice! It also claims that the DR DOS equivilents of SMARTDRV.EXE and HIMEM.SYS that Windows 3.1 installs are superior, so you should remove these from your CONFIG.SYS.

I extracted the ZIP to a disk image, then ran the update. Note the space; the parameters are for the target drive, and the target folder:

A:\> UPDATE C: DRDOS

Donezo. I restarted, ran SETUP.EXE again, and success!

Finishing up

The installer proceeded as normal, and I was left with a familiar Windows 3.1 desktop. I’ve installed drivers, applications, Central Point PC Tools, and the Windows Entertainment Pack, and have had no problems whatsoever.

Certain Windows applications require SHARE.EXE to be running, which DR DOS also includes:

:: AUTOEXEC.BAT C:\DRDOS\SHARE.EXE

I let the Windows for Workgroups setup detect applications already installed on the system, which lead it to create shortcuts for the default XY Write tool invoked with EDITOR, and an interesting screen locking utility:

I also took the liberty of rebranding Program Manager, and the MS-DOS Prompt to something more DR DOS-like. Seeing that VER string in a window on Windows 3.1 is such a damned novelty, I can’t help but grin!

I think I might have a new favourite pre-Windows 95 environment. DR DOS 6.0 feels like it boots faster than MS-DOS 5.0 (the closest analogue from Microsoft), and the tools are more sophisticated. But that’s for another post.

If you scrolled to the end and didn’t want to read the journey, get a copy of the DR DOS 6.0 Update for Windows 3.1 and you’ll be good. Or run DR DOS 7.0, which I assume has these patches pre-insalled.