MULTIBOOT WINDOWS

w3.1 - 95 - 98 - ME - 2K - XP - 6 - 7

I own numerous old PCs running a mix of DOS-w3.1, w95, w98, XP and later.

Out of curiosity I've been doing some testing on multi booting w9x to see what's possible.

I started off testing multi booting by not using any boot manager and while that method will certainly work for simple installs, I discovered some excellent small DOS-Windows boot managers (OSL2000, XOSL, BootitNG) that simplify the process and make it much easier.

I've found it is possible to multi boot combinations of DOS-w3.1, w95, w98 and ME (and also other versions such as Windows 2000, XP and 7) in either dual, triple, quad or quad+ boot versions - although depending on the number of OS's to be booted and their boot architecture, there are a few quirks to be overcome.

Also note that the multi boot examples on this web site and explanation(s) thereof only apply to versions of Windows that can be installed using the MS MBR (or in some cases, an extended MBR) partitioning scheme.

After a fair bit of futzing around, I've been able to:

Dual boot Windows 95 and 98 no boot manager used
Dual boot Windows 98 and XP using XP boot manager
Triple boot Windows 98, XP and 7 using XP+w7 boot managers
Triple boot Windows 95, 98 and ME using shareware BootitNG
Quad boot 4 themed installs of w98 no boot manager used
Quad boot Windows 3.1, 95, 98 and ME no boot manager used
Quad boot Windows 3.1, 95, 98 and ME using freeware OSL2000
Quad boot Windows 3.1, 95, 98, 2000 using freeware XOSL
Quad boot Windows 2000, XP, Vista, and 7 using Windows boot managers
Quinta boot Windows 98, ME, 2K, XP and 7 using shareware BootitNG
Octa boot 8 XP installs on 1 x 2GB VHD using XP boot manager
Undeci boot 11 Small Windows XP Versions using XP boot manager
DuoDeci boot 12 installs of eXPerience XP using XP boot manager
FAT16 Multi 8 FAT16 installs (w3-Server 2K3) using BootitNG

which include various combinations of DOS-w3.1, w95, w98, ME, 2000, XP, Vista and 7.

Generally, the more OS's added to the mix the more quirky it becomes, due to w9x versions over-writing each others boot files. Using a boot manager such as OSL2000 simplifies things, although it is still possible to multi boot without a boot manager.

DOS-w31 with w9x installs adds another complication as w9x installers insist that partition 1 for their boot files be FAT32 and not FAT16, but this can be overcome with most boot managers.

Multi booting w9x with later Windows versions is relatively simple, as these OS's are multi boot aware. Just use the "oldest-first / newest-last" install approach for Windows manual installs done not using a boot manager.

I've been testing out various combinations of w9x using VirtualBox 6.1.26 and this website has all the multiboot VirtualBox VHDs I've listed above (and also uploaded to the Internet Archive).

All the installs on this site were done in Virtualbox simply to demonstrate what's possible and to allow you to download the VHDs and try them out yourself in Virtualbox.

Just for SnGs I've done most of the dual, triple and quad boot installs here on bare metal builds. Easy peasy.

Multiboot - Example VHDs and Tips:

To see details of all the multiboot Windows VHDs I've created so far (and also download) . . . click here.

To explore the pitfalls of multibooting Windows 9x based on advice I received from Dr. Web . . . click here.

For my conclusions (so far) on the Windows multiboot experience (and some quirks thereof) and also my experience with using various boot managers (namely OSL2000, XOSL and BootitNG) . . . click here.

For details on what's probably the quirkiest way to install an OS in VirtualBox (or any VM) . . . click here.

For the easiest way ever to install either DOS 6.22 or Windows 3.1 from a CD . . . click here.

To visit my Internet Archive site that mirrors most of what's on this site . . . click here.

A tip for multiboot installs of later Windows versions (w7-8-10-11):

Use DISM to apply the Windows image directly to a partition and then update the Windows BCD store on the
boot partition with a tool such as NeoSmart's EasyBCD or BoYans VisualBCD - or the Command prompt for all
you diehards.

Using DISM allows for a quick Windows install and I now use it for my w7-10-11 multiboot installs. I wish I'd
discovered it 5 or 10 years ago but better late than never.

Final thoughts on multibooting:

Everything on this site is a result of my experience multibooting Windows, from w3.1 and w9x (w95-w98-ME) through 2000, XP, Vista, 7 and 8.

The biggest take-away after doing this, and the best advice I can offer to anyone, is that if you want to boot two or more versions of w9x (or DOS-w3.1) then do it the easy way and use a boot manager (such as OSL2000 or XOSL) and avoid the hours of frustration with w9x over-writing common boot files.

Both OSL2000 and XOSL are free products and handle multiple DOS-w3.1-w9x installs just fine (although are a little clunky for 2000-XP-6-7-8 installs).

If you only want to multiboot Windows 2000-XP-Vista-7 then do it the easy way and use the standard Windows installers as these are multiboot aware - always install going from old to new, 2K->XP->Vista->7.

And if you really want to stretch multibooting and install every Windows version on one hard disk, then use the BootitNG boot manager which can install to multiple extended primary partitions (15+ at least), although be aware this is a shareware product (but the license is relatively inexpensive).

However, if you just want to explore multibooting for yourself and find out what works and what doesn't work, then do the same as I did and install VirtualBox or VMware, download some boot managers (as there are quite a few around) and try them out and see what works for what you want to do.

From my own experience, every hour spent testing your multiboot plan in VirtualBox or VMware will save about 5 hours of frustration in the real world.

Testing in a virtual machine will be a lot quicker than testing on a physical machine and different install approaches are easy to try out - and there's the added advantage of being able to take a snapshot as you go so that if one step doesn't work you can revert to a previous snapshot and try something different.

Even if you're still running Windows XP, VirtualBox will run on XP 32-bit up to version is 5.2.44. The last Oracle certified version for XP, i.e., guaranteed to work, is 5.0.20 but I've found all v5.n.n work fine on XP.

Check my FTP server for some selected portable versions of VirtualBox in the folder:
..\FTP_HOME\034_VirtualBox_Portable_Versions_for_VHDs

or for the the complete VirtualBox collection, including some versions by Innotek for Windows 2000, go to:
..\FTP_HOME\000_Freeware_DLs_CATG_2007-25_530GB\Virtual_PC\VirtualBox_(Sun)

For all FTP newbies out there, you can download a small portable FTP client that comes pre-configured with options for several FTP sites, including mine (Shotter_Nails_FTP_Site), by clicking . . . here. Unzip and run.

The bottom line to all this is that you can multiboot any version of Windows in combination with any other version of Windows - you just need to plan out what you want to achieve and pick the right tool for the job (or in lots of cases, no tool at all other than the Windows installers).

Try out multibooting with VirtualBox or VMware - when you suss it out you'll be as happy as a dog with 2 tails.

Kind regards,
Shotter_Nail

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