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I have an old Pentium II computer, and I would like to set it up as a retro gaming machine, but I would also like to play around with old distributions of Linux, OS/2 and other operating systems.

What would be a good way of setting it up in such a way so that I can have multiple "instances" of old operating systems installed at the same time, such as an "instance" of MS-DOS with Windows 3.1, another "instance" of MS-DOS with some other software, an "instance" of Windows 98, etc?

I was thinking about using SD cards, or laptop HDDs with an IDE to SATA adapter, but I would need a lot of them, which isn't ideal. Also, constantly disk imaging would be pretty inconvenient.

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    Some of us happily had multiple operating systems on our original Pentiums. I went for DOS and OS/2, very easy. At the time most games used DOS, not Windows, to maximize memory.
    – Jon Custer
    Jun 5, 2023 at 14:33
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    ide2cf or ide2sd boot device and installing each system on its own card cards. The PC itself can still have common partitions that are accessible from each boot card. Multi boot systems on one disk were a pita then, no need to endure that pain now. Jun 5, 2023 at 15:34
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    Install a boot manager? Depending on OS support and BIOS there may be limitations how big partitions are supported by the OSes though.
    – Justme
    Jun 5, 2023 at 20:14
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    If you really want to ogg it, you could put dozens and dozens of systems on one pc. Although this approach is likely way too involved if you're just looking to run three or four systems, I couldn't resist mentioning it. :-)
    – noughtnaut
    Jun 6, 2023 at 7:29
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    I once ran Windows 3.1 and a version of linux on a 386. I did it by modifying config.sys to give me a choice when the machine booted. That is about all I remember about it.
    – Wastrel
    Jun 6, 2023 at 13:02

9 Answers 9

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I would use partitions on a large hard drive, with something like Ranish Partition Manager to choose an operating system while booting. This supports quite a few different partitions, with the ability to hide irrelevant partitions to avoid one operating system damaging another. This will allow you to try pretty much any PC-based operating system.

It is possible to shoe-horn some combinations of operating systems into a single partition; for example, you could install Windows 98, and then patch it so that it can run Windows 3.1 as well. A CONFIG.SYS menu can then be used to choose between plain DOS, Windows 3.1 and Windows 98. Likewise, OS/2 can be installed on a DOS partition and set up so that you can choose between OS/2 and DOS during boot. Older distributions of Linux can also be installed on a DOS partition (using UMSDOS) and booted from DOS (using LOADLIN). In practice however I would avoid complex setups like these and just use different partitions (except, perhaps, for DOS/Windows).

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    If Linux is one of the operating systems installed, then its boot manager (probably LILO for a Pentium II era machine) will be able to boot from the other partitions. LILO can also remap drives at a BIOS level allowing partitions on secondary hard drives to be booted.
    – john_e
    Jun 5, 2023 at 20:17
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    I agree with Stephen, but would suggest that Partition Magic would be worth looking at since various tools were written with the active participation of Linux filesystem etc. developers. Try to avoid anything that's dedicated to a particular brand of drive etc., since even if Linux is supported the relevant programs might need binary-only modules which are tied to a limited range of kernel versions. Jun 6, 2023 at 5:58
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    FWIW when I used to multi-boot back in the day (and now on my PIII machine) I always found the BeOS boot manager to be very easy to install. You don't even need to install BeOS, you could run the live Personal Edition and just run bootman to install it.
    – Matt Lacey
    Jun 7, 2023 at 11:12
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    @MattLacey Even as short as it is, I think that's worthy of being its own answer. Jun 7, 2023 at 17:06
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I use SD cards because they result in less "constant disk imaging" than other solutions. In fact, ever since being clued into the idea by an LGR video, I've been migrating all my machines over to using SD cards so it's easier to add new OSes to play with as I acquire them. (My P1 133MHz machine is set up to boot MS-DOS 6.22/Windows 3.11 for Workgroups and Windows 98 SE and only has room for one more OS, but I've since acquired DR-DOS 6, Novell DOS 7, QEMM 97, the Windows 3.1x resource kits, and various other things I want to have fun with.)

Given that 16 gig SD cards are already bigger than I need, and how inexpensive "small" brand-name SD cards of sufficient performance can be, I think the only approach that would involve less re-imaging would be something involving sticking a PCI gigabit NIC with PXE firmware into your machine and netbooting it off disk images stored on your modern PC. (Something I may do once I have time to look up a good replacement for my 100Mbit NIC that still has DOS packet drivers. I already added a gigabit NIC to my Lenovo 3000 J Series just for the speed.)

However, if you do want to split a single non-removable drive into multiple OSes, Stephen Kitt's advice to use a boot manager is the way to go. I forget which open-source one I had trouble with (The AST Adventure! 210 is also prone to freezing MEMMAKER and refusing to boot with a Voodoo 3 3000 PCI in its only PCI slot), but the copy of IBM Boot Manager included with my childhood copy of PartitionMagic 3 works just fine.

(If you can snag a used copy of PartitionMagic, it's also got a nice little command-line utility with DOS and Windows NT versions named PQ Boot which implements "change active boot partition and reboot" so you can extend Windows 9x's "Reboot into MS-DOS Mode" paradigm into completely separate OSes as long as you've got something on the other end to swap the active flag back.)

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    Worth noting an issue with SD is the wear-out on write - I've only really had an issue with it running a home automation system that was logging data constantly, it would kill an SD card in like 6 months, which has made me particularly sensitive to the problem. Not a reason not to do it, especially since this use case is vastly different, but just know the data is relatively fragile compared to other mediums, so probably be vigilant with backups if you care.
    – James T
    Jun 6, 2023 at 10:34
  • @JamesT that depends way more on interval written (number of writes per time) than amount of data. Beside that, for somewhat modern SD it's the very same technology than with any SSD.
    – Raffzahn
    Jun 6, 2023 at 20:03
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    I had one of the SD cards in my OpenPandora palmtop PC hit its write limit after six or seven years. Assuming you don't have a no-name SD card and the flash controller doesn't die, wear-out should present itself as the card locking itself as read-only rather than becoming inaccessible... so I would say that, for a use-case like this, aside from any progress in whatever game you were playing at the moment it locked, SD cards of comparable quality should need backups as much as any other medium but not uniquely more so.
    – ssokolow
    Jun 6, 2023 at 23:39
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When you install Linux, it will come likely with LILO or GRUB or some other boot manager that you can use to select operating system at boot.

Often when you install Windows though, it will wipe out your boot manager from MBR. So you have to have a bootable recovery USB to reinstall the boot loader when needed.

It may make sense though to try running these games in virtual machines or using DOS emulator and wine for windows. Unless you are more interested in making these old stuff work than actually playing.

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Another possibility, which would fit well with a "retro" feel, would be to find some kits that install 3.5" hard drives in carriers that then mount with a socket in a 5.25" drive bay, and have such a socket connected as the first hard drive. Using such sockets would ensure that there would be no possibility of an operating system that doesn't understand modern hard drives accidentally erasing data from some other OS install, because it would "own" everything on the first hard drive, and even if one OS disk got infected with malware it would be unable to covertly access anything associated with any other OS.

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  • Bear in mind, that's basically the bulkier, but more retro-authentic approach to what I and Clint from LGR do using an IDE-to-SD Card adapter that installs into an expansion slot... but thanks for reminding me to put that on my "things I wanted as a kid and can now eBay" list. (The list that saw me buying a floppy drive lock a few years ago.)
    – ssokolow
    Jun 6, 2023 at 23:41
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The answer depends a bit on whether you are keen to experience true 80s feeling with the constant (enjoyable?) background turbine noise of a moving hard disk.

Physical disks will need to be partitioned to be able to hold more than one operating system. Early systems very rarely did respect basic common co-existence rules, however, especially regarding the boot sector and partition table. Many OSs will simply overwrite the boot sector to boot into their just installed partition during installation, which can be very annoying. Some might simply flatten the whole disk on install. So, when selecting a partition/boot manager, make sure you use one that allows you to "hide" partitions from the system to protect them (Symantec's Partition Magic used to be the tool of choice back in the day). I tend to use plop, which adds some other nice features to the boot like booting from USB or CDROM even on systems where the BIOS doesn't support that.

Another nice option is, as you said, using removable media like CF or SD card adapters. Both can be purchased very cheaply and will connect either to the ISA bus (like XT-CF, for example) and will come with BIOS extensions, or connect to the IDE connector of the main board directly. Make sure you purchase a model that exposes the card slot through the ISA bus back panel. You can easily have multiple dedicated cards per operating system install. Backup and restore of an install is also particularily easy (I simply use dd to and from a NAS to backup the images).

Even if you decide to use a card-based solution, a boot manager like plop stil makes a lot of sense due to the additional boot options they implement.

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One thing I used to do was to have multiple hard drives connected to an IDE selector switch. You connect several drives to it and it exposes one of them to the computer based on which button is pressed. This makes it fairly easy to switch between drives without having to open up the chassis and move cables around.

This had some distinct advantages over using multiple partitions on a single drive. There was no complicated bootloader to configure. Some old OSes had issues if they were on an "extended" partition. Some didn't play well with others on a multi-partition system (Windows in particular was notorious for hijacking your bootloader and erasing any mention of a non-Windows OS). With a drive switch, each OS saw itself as the sole OS on the system, and there were no problems with systems interfering with each other. Getting your hands on a switch like that might be tricky, but nothing says retro like a nice, chunky rotary dial.

If you go the multi-partition route, I'd like to second Matt Lacey's comment about trying the BeOS bootloader. It's delightfully uncomplicated and supports practically anything you want to boot with it. Chapter 3 of The BeOS Bible talks about the boot manager setup process. Just boot into the live "BeOS R5 Personal Edition" and run bootman in the terminal. A version of Partition Magic is also included in it. Side note: If you've never used the BeOS operating system, I highly recommend that you add it to your list of retro systems to toy with. It's an absolute gem, ahead of its time in many aspects, and runs well on low-spec hardware. Definitely one of my personal favorite retro platforms.

Another workaround for the multi-partition use case is to install your boot loader onto a floppy disk instead of the hard drive. This will give you a "boot floppy" for booting a particular operating system. I had a system that had Windows 98, BeOS, and Linux (probably Slackware) installed on different drives/partitions. Windows wouldn't play nicely with the others, so I let Windows install its own bootloader on the hard drive and then installed the BeOS bootloader onto a dedicated floppy disk. If I wanted to run something other than Windows, I'd pop in the boot floppy and the system would boot to a nice menu where I could select an OS. Take out the floppy and the system booted straight into Windows.

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so that I can have multiple "instances" of old operating systems

The main issue here might be that not al old OS can easy coexist with each other. It's usually possible as newer they get, but some (looking at you Windows) have still some hassles up the sleeve.

I was thinking about using SD cards, or laptop HDDs with an IDE to SATA adaptor, but I would need a lot of them, which isn't ideal.

IMHO that is the least problematic setup as each OS will have it's own disk (As SD or CF on an IDE adaptor), removing any need to make them well behaved. Maybe having a secondary drive with FAT format for easy file exchange between . That is, of course, unless fiddling with setup and cursing for hours is your favourite wate of time :))

Also, constantly disk imaging would be pretty inconvenient.

It would. CF or SD may simplify that a lot.

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I'll throw my suggestion in. I started using XFDISK recently which is a better fdisk than MS-DOS fdisk. It can manage partitions and installs a boot manager that is dead simple and installs on the boot track, requiring no partition of its own and no files on any partition. The program itself runs in DOS, but that's only to set it up or to add a new entry. I'm sure there's better ones, but I like that it doesn't require a 386 and is barebones simple. And it just works.

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What I used to do in the early 90s was to have a 2 drive system: one fixed and one removable. The removable drive was the bootable drive. I used 4 - one for Linux, one for Windows with the office tools, one for Windows with development tools, one for kids games. The kids' PC was more powerful than mine so if I wanted faster processing I'd move my caddy to their machine. The fixed drive contained the data which would be accessible, whichever boot drive was used.

All the removable drives had to be the same size so the BIOSs wouldn't go crazy every time they were switched.

If you can get hold of old disk caddies, they're ideal for this. Just install your different OSs on the removable drives. There is no need to worry about one OS corrupting another or which one to install first.

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