How-to Triple-Boot Windows, MacOS, Ubuntu and a shared DATA partition on the same disk

Preamble :

As Apple now turns to ARM processors for their MacBooks, killing BootCamp as a concept, then I though I should just make a short how-to install multiple OS’s on the older, soon to be considered useless, computers as they will probably be very affordable.

Apple created the official BootCamp concept for OS X Leopard 10.5 in 2007. They released an official installer to install OS X and Windows. However they chose to make it a hands-off installation which did not use the full potential of the concept.

Apple kind of killed BootCamp when introducing macOS High Sierra in 2017. The important feature of the Hybrid MBR scheme were no longer included in Disk Utility. This does not mean that BootCamp cannot be used with newer macOS versions up to and including macOS Catalina released in 2019. It is just more complicated to install.

Why bother :

The procedure I will outline allows to install :

  • Windows 7 or 10 on a NTFS partition.
  • MacOS up to and including High Sierra. If the computer supports Metal then also Mojave. Catalina can be installed too but is somewhat tricky to install. Newer macOS’es will not work.
  • A shared DATA or MEDIA partition on a NTFS or exFAT partition.
  • An Ubuntu installation with a root and a swap partition.

The benefit here is that you get two Windows accessible partitions instead of one. You can use them for whatever you want. I prefer one separate partition to hold DATA.

This requires five partitions and with some hidden extra partitions for boot and recovery that makes for seven partitions.

Introduction :

The description below sometimes refer to OS X and sometimes to macOS. It is just left-over noise from revising the text the number of times.

BootCamp as a concept is a slightly fragile mix of a disk simulating having been initialiased as a MBR disk yet really being a GPT disk. The first four partitions created on the disk will have a MBR identity. Additional partitions will not have a MBR identity, only a GPT identity and can only been seen by OS X and Ubuntu.

The difference from the official installation method is that one should make the partitioning from an OS X ( macOS ) Installation DVD ( sort of .. ) simply using Disk Utility.

The Disk Utility program included in OS X and macOS will automatically create the Hybrid MBR support when a partition is created that is a Windows type, like FAT or NTFS. Simple as that. But notice the last version to have this feature was Sierra. The disappearance may be related to the introduction of the APFS file system introduced in High Sierra.

It is still possible to install support for the Bootcamp concept on computers intended to run High Sierra, Mojave or Catalina. It just requires using a Sierra version of Disk Utility to do the disk partitioning. No OS needs to be installed on the disk for this to succeed.

The MBR setup allows for four primary partition. We need a primary partion to boot Windows. The official BootCamp install tool from Apple installs OS X in the first partition before Windows. This is silly as the OS X recovery partition will take up a partition wasting a precious MBR partition ( seen from the Windows perspective ).

The official BootCamp concept installs OS X in the first partition before Windows. This is silly as the OS X recovery partition will take up a partition wasting a precious MBR partition ( seen from the Windows perspective ).

When you start partitioning you select to initialize the disk as GPT ( called GUID by Apple ). Disk Utility will silently create a small EFI boot partition as first partition. It will just be there. The first -official- partition to create should be the NTFS Windows System partition. The second should be the NTFS DATA partition. And the third partition should be an HFS+ journaled case insensitive partition. That defined the four MBR partitions and completes the operations for which Disk Utility is needed.

TIP : Having the HFS+ partition as the fourth MBR partition allows Windows to access the content of the HFS+ partition provided the proper driver is installed. If this feature is not needed then yet another NTFS partition could have been created instead, effectively moving the HFS+ partition outside the MBR visible range.

Remember to leave un-allocated space after the allocated partitions so Linux can be installed. And also leave some space to allow raw disk cloning ( see below ). A reasonable figure would be 10..100 GBytes.

You can now install whatever (*) flavour of OS X ( ~ macOS ) you want onto the HFS+ partition. OS X will silently resize the HFS+ partition to add a partition for recovery. It does so without destroying the MBR mapping and without taking up a MBR partition ( if installed as the fourth partition ).

(*) Whatever means up-to and including Mojave. Using the recommendable mac program CCC, it is possible to install Mojave onto a HFS+ partition. It is not very easy, but do-able. Catalina do require an APFS formatted disk and it does not support the Bootcamp concept at all nicely. The way to install Catalina is first installing it to a single partition spare disk and then use CCC to copy the content over to the HFS+ partition on the main disk with the multi-boot partitions. CCC will convert the partition to APFS. You may loose the boot manager for Windows if you had already installed Windows. It is fixed by installing a dummy Windows 10 installation to the DATA partition. It will recover the boot manager and also install Microsoft dual boot between the Windows OS’es. You can then delete the new Windows 10 if you don’t want it.

To summarize :

  • Up to and including Sierra. Use the included Disk Utility for partition the disk. And install OS X or macOS in the 4’th partition.
  • High Sierra must be partitioned using the Sierra Disk Utility ( or older ). The mac format can be HFS+. No trouble.
  • Mojave is like High Sierra except that Mojave will re-format its partition to APFS if installed to a SSD. This can be tricked by installing to a classic harddisk and then use CCC to copy the installation to the SSD keeping HFS+. No trouble except it takes extra time and requires CCC.
  • Catalina is like Mojave except there is no way around APFS. This will for some reason kill the Windows boot information if Windows were already installed. This boot problem is solved by installing a dummy Windows 10 installation on the DATA drive ( the 3’rd partition ). This will fix the boot problem of the main Windows installation ( on the 2’nd partition ). The dummy can be removed afterwards.

Thereafter you can install Windows. Windows will see the disk as a basic MBR disk. Nothing special. Finally you install Support for BootCamp in Windows.

Support for BootCamp is actually nothing more than hardware drivers and a utility one to configure the BIOS, selecting whether you boot to the Mac boot disk selection menu, or boot directly to Windows.

Thereafter you can install Ubuntu. It will install itself by accessing the disk as a GPT disk and use some of the un-allocated disk space. It will recognize that you have Windows installed and offer to install a GRUB boot menu that offers to boot either Windows or Ubuntu. I prefer using that option.

Booting between the three OS’s is therefore something like this. Either boot to OS X selection or Windows/Ubuntu selection as programmed into BIOS. That BIOS setting can be modified in OS X Preferences and in the Windows Task Bar. If you see the Windows/Ubuntu selection then you can choose which OS to boot. There is a default timeout which in effect allows the computer to boot to Windows or Ubuntu without human interaction.

Corrupt Partitioning Check ( rEFIt 0.14 ) :

The dual partitioning mapping ( MBR and GPT ) can get out of sync. I haven’t experienced this for years but it was quite normal to happen in the early days. It is therefore important to verify that the two tables are in sync. There is a utility to check this, called rEFIt 0.14. It is a nerdy thing, yet easy to use, that runs under OS X. Download it and do a check. rEFIT cannot run on Catalina though.

Backup :

There is really no safe way to backup this tricky disk system configuration using a backup program. So I do something different. I make a complete disk copy ( ~clone ). To do so you must have ( at least ! ) two identical disks. Or spare disks which are the same size or somewhat larger than the currently used. Look for the number of sectors. Not just the number of GBytes.

Cloning is effectively done, booting into OS X Recovery Mode.

First un-mount the clone disk ( if mounted ) using Disk Utility.

Then get the disk numbers and use DD to clone the disk using a Terminal window. Use the procedure listed on the following web site to do the actual cloning ( yes it is from 2011 ) :

Unix Geekery: Cloning a Dual-Boot Hard Drive With dd

See the Clone Your Hard Drive section there for the required typing. It is marked in red for your convenience. It is only a few lines that needs to be typed.

You clone the whole disk in one operation. Not the individual partitions.

Hint – You may need to use the Caffeinate command to prevent the computer from going into sleep while cloning.

I have used DD for years as there were no reliable alternatives. Nowadays there are utilities for MacOS that claims to handle the hybrid partitioning scheme. But why bother ..

Updating :

Updating/refreshing each OS is no different from what one would do if there were only one OS on the disk. I even made an in-place update to Windows 10 from Windows 7, back in 2015. It just works.

The recently ( April 2022 ) introduced Ubuntu 22.04 Jammy is said to remove Windows from the boot list managed by Grub, forcing you to do some manual steps. This is however not true for MacBook Pro’s. No problems.

Summary :

This is the old school way of managing multiple OS’s on one disk. Modern people prefers virtual environments like VMware. VMware player 15 ( the current version at this writing ) is quite reliable but I prefer the real thing.

How-to Install Win 3.11, Win95, Win98 and Win2000 on the same MBR disk

Preamble :

I recently had to start my very old laptop to open a WPK file ( that is the original Wordperfect file format ) using the program installed under Windows 3.11. Which made me reflect a little about that computer. So here is something from memory lane.

Nowadays I only run Window 10.

But I also keep an aged laptop running Window 7 and Windows XP. It doesn’t see much use, frankly. But better safe than sorry so I keep it.

And I keep an even older laptop from around 2000 running Windows 3.11, 95, 98 and 2000.

Uncommon Disk Configuration :

Having a single computer switchable between those four old OS’s is not common. And it also requires a special partitioning scheme that Microsoft actively disapproved stating it would give trouble and did not support doing. I haven’t experienced any trouble.

The key to allow this is partitioning the hard drive with four primary partitions.

In those days most disks was IDE disks ( contrary to now SATA ) and the disks used the MBR disk initialization scheme ( contrary to now GPT ). The disks sold those day could be as small is 6GB. The sweet spot disk size for this setup is 40-80 GB. Odd problems could arise using disks larger that 128GB so don’t do that.

It can be difficult to find a utility that allows doing this special partitioning. But companies like Paragon and Acronis had disk utilities that supported doing this off a boot CD. I used such tools.

While writing this, I googled the subject and found a link to a free utility which claims to support generating multiple primary partitions.

See here :

Otherwise you could mount the disk in an external enclosure to do this. If you have an older Mac then Disk Utility can be used.

Disk partitioning could/should be done before installing any OS. Just in case something should go wrong.

How to select the OS to boot :

The tool used to switch between which partition to boot from is the very basic tool FDISK.exe which was included in all DOS versions. You select which partition should be Active next time you boot. Simple as that. Windows 2000 has a GUI to set the Active partition but the principle is the same. Notice though that FDISK with DOS 6.22 ( Windows 3.11 ) can see and select all primary partitions but it doesn’t know what is on the partition and it also reports the partition size wrongly. But selection works.

No need to install any fragile custom boot manager or anything. Any computer savvy person can do this.

Using this concept has the very nice property that the active disk is always given drive letter C:. The drive letters for the other partitions were mangled in a way only Microsoft could explain. Or maybe they could not.

Remember that Win 3.11 could only install on FAT. 2GB max. And it could not understand any newer partitions like FAT32 nor NTFS. So one such partition should be made. I made it the first partition on the drive. Some also claimed technical reasons for why a FAT partition should be created first.

The next two partitions were for Windows 95 and 98. They also supported FAT32 but not NTFS. So FAT32 were used. 4-8 GB were the sizes I choose.

Finally a partition for Windows 2000. It supported the older partitions and NTFS. I preferred to use FAT32 because then Windows 95 and 98 could use drivers located on that partition. So this partition was the largest. Which was nice as it could also be storage for backups for the older OS’es.

Installing these OS’es requires old hardware. Old hardware is not supported well by newer OS’es. In particular, don’t install Windows XP instead of Windows 2000. It might install but will disappoint because it really requires faster hardware.

Installing and Round-Up :

All four OS’s were fully independent and did not rely on each other. So once the drive were partitioned then each OS could be installed in any order. The benefit of that fact was that it was also easy to backup each partition to support recovering from system corruption often occurring when installing drivers for the three oldest OS’es. Windows NT backup was very handy for this.

I strongly suggests that a partition backup is done after every driver installation with the older OS’es. If a driver installation fails, and it often does, then your installation on that partition could be in an corrupted state. Being able to recover/restore is a major convenience. Always restore and try again, if something unexpected or unexplainable happens during driver installations.

Then it was time to actually install an OS. While partitioning the disk one should also have made the decision which partition to boot from. Which OS to install first. Suggestion is starting with Windows 2000 to have the backup utility ready when installing the older OS’s afterwards.

There is essentially nothing more to this subject. The concept described is very robust contrary to Microsoft’s officiel dual-boot concept which often corrupted the OS’es if anything unexpected happened.

Well, maybe one more advice. Do yourself a favour and install a dual pane file manager. For DOS it would Norton Commander or a similar free tool. For Windows it would be Windows Commander ( ). Life is so much easier using these tools during the driver installation phase.

DOS Boot CD :

It is nowadays possible to boot to DOS from a boot CD. Using a boot CD instead of a floppy disk gives a boot speed advantage. It also allows to boot a system that does not have a floppy drive at all. That was the case for several laptop models from around year 2000. Those laptops were sold with an external floppy drive that connected using either the printer port or an USB port. Fortunately the BIOS for those machines often also supported booting off a CD :

Look here for ISO images :

Start Menu for Windows 3.11 :

You can actually download a program called Calmira II that gives Windows 3.11 a start menu like Windows 95. That is the coolest thing I have seen for years :

Look here for info :

Laptops from around year 2000 :

What is a usable laptop from year 2000 to implement this four OS scheme. A relevant question as they cost next to nothing if they can be found.

There are three essential qualities for such a computer :

  • It must have a proper graphics chip. The ATI Rage or derivative is a good starting point. Besides having Windows drivers for Win 3.11 and newer it also supported DOS graphics.
  • It should have a proper sound chip. The ESS Maestro in some variant is a good starting point. Besides having Windows drivers for Win 95 and newer it also emulated Sound Blaster Pro in DOS and Win 3.11.
  • It should have a BIOS setting to expand the display to full size in text DOS. Otherwise the DOS display will only cover the central part of the display which looks silly.

Using USB for anything pre Windows 2000 is hit and miss, except for an USB mouse on Windows 98. These old laptops usually had only one USB 1.1 port anyway. Be sure to have backups before trying to install USB drivers.

Examples of compatible laptops includes : Compaq Armada M700, HP OmniBook 6000, Dell C600 and IBM ThinkPad 20-something. They are rare, fragile and probably ugly. And they were expensive when new.

As a compromise there are still plentiful of ThinkPad 40 and 41. The ThinkPad 40 and 41 are quite simple to install if they are fitted with the Radeon 7500 chip. The ThinkPad 41 with a Radeon 9000 chip can be used for Windows 95 using a UNIVBE display driver. But it only supports generic 16 color VGA for Windows 3.11. And there is no sound support in Windows 3.11.

The best ( in the meaning of giving the fewest complications ) computer to configure for a four OS setup would of course be an old desktop computer with a Tseng ET4000 graphics card and a Creative Sound Blaster sound card.