Do's and Don'ts of installing multiple OSes on MacBook Pro Late 2011

I have successfully installed macOS High Sierra, Windows 10, and Ubuntu 20.04 on MacBook Pro Late 2011, and there were some challenges worth noting down.

Formatting the disk

When booting into recovery mode to format the disk, the installation USB used must be of an OS X (Mavericks, for my case), not a macOS (newer version). I once booted into recovery mode using macOS High Sierra installation USB to format the disk with GUID Partition Map scheme, and then I was unabled to install Windows 10 through VirtualBox. I got the error message "The selected disk is of the GPT partition style." when selecting a partition to install Windows on. 

This is because I tried to install Windows using legacy mode and then Windows required a MBR disk, but it was GPT disk. However, when I booted into recovery mode using OS X Mavericks installation USB instead to format the disk with GPT Partition Table cheme, the error message was gone. Why? because the disk was hybrid MBR, not pure GPT, and so Mac OS saw it as GPT but Windows saw it as MBR. As Windows did not support EFI mode at that time, Apple used hybrid MBR to allow users to install Windows on its machines that used EFI boot.

Partitioning the disk

The disk must be partitioned as needed before installing any OSes on it or one of the OSes won't boot after the partition is resized or a new partition is created. 

At first, I didn't do that. After installing macOS High Sierra and Windows 10, I created another partition from the Windows 10 partition and then Windows stopped booting. It's because of the OS's boot entry is missing from the MBR, and I don't know why but this post claimed to fix that using a third-party tool. Unfortunately, I've never succeeded.

Ordering the partitions

In my case, I have 5 primary partitions:

1. EFI system partition
2. macOS
3. Windows
4. DATA
5. Linux

The first partition was hidden and created automatically by DiskUtility so I shouldn't have mentioned it but this is to show that the DATA partition must be the fourth partition so that it would appear in File Explorer (as I wanted) when booting into Windows. If it was the last one, it wouldn't show up. This is because the disk was MBR to Windows and so it could have only four primary partitions. Windows recognized only the first four partitions and ignored the rest so Linux partition was treated as unallocated space (this can be checked in Disk Management).

In DiskUtility (of OS X Mavericks), the first partition is graphically on top. Since the EFI system partition is not visible in DiskUtility, the macOS partition is on top instead.

Installing Windows using BIOS legacy mode without CD-ROM

Since my CD-ROM drive stopped working a long time ago, I couldn't install Windows with Boot Camp Assistant because my machine, by default, only looked for Windows installation files from the CD-ROM drive but it couldn't find it. 

When I forced the machine to look for the Windows installation files from a USB drive (by holding down the Option key while it's starting), it worked but Windows was installed using EFI mode instead, and the problem with EFI mode is the external monitor is not detected on Windows. This problem only happens on my Mac model, not the newer ones.

Everything worked fine when installing Windows using BIOS legacy mode, and the workaround was installing it through VirtualBox. I noted it down here.

How to clone Ubuntu OS partition?

I'm using Macbook Pro 13-inch Late 2011 running Ubuntu 20.04. I used the built-in application called Disks to backup the Ubuntu system partition into a disk image (*.img file) and then restore the disk image back to the partition.

IMPORTANT 

• When backing up a system partition, the EFI system partition should also be backed up if it exists (using either Disks application or cp command)
• The backed up or source partition must be smaller than or equal to the destination partition
• The size of the disk image (*.img file) equals the size of the (backed up) source partition even if the partition has free space. The source partition should be resized as small as possible so that the resulting disk image is acceptably small.

To Backup

Backing up Ubuntu partition:

• Boot into Ubuntu Live (on USB) and chose Try Ubuntu

• Open Disks application from the menu (press Windows key and type Disks)

• Select the partition to backup 

• (Optional) Click on the settings icon for more options and select Resize

• Click on the settings icon for more options then select Create Partition Image...

• Make sure the file name and location are correct. The partition for storing the disk image must be mounted or it'll fail with a message like there is not enough space or something else confusing.

Backing up EFI system partition:

The EFI system partition is where the Ubuntu bootloader locates in because I manually chose the partition for the bootloader while installing Ubuntu (It's a must to install Ubuntu using EFI mode).

I used the method above to clone (backup) this partition, and also manually copied its content using cp command. Of course, using cp command is simpler and works just fine. The partition has only one directory named EFI.

> sudo mkdir /mnt/sda1
> sudo mount -o loop /dev/sda1 /mnt/sda1
> sudo cp -rf /mnt/sda1/EFI /media/myusb/ubuntu-efi/

To Restore

Restoring Ubuntu partition:

• Boot into Ubuntu Live (on USB) and click Try Ubuntu

• Open Disks application from the menu

• Select the (destination) partition for running Ubuntu 

• Click on the settings icon for more options and select Restore Partition Image...

• Browse to the (source) partition that the disk image (*.img file) is stored on

• Select the disk image file and click Start Restoring

Restoring EFI system partition:

I opened Terminal and used the cp command to copy it back from the USB drive to the EFI system partition (in my case, /dev/sda1). 

> sudo mkdir /mnt/sda1     

> sudo mount -o loop /dev/sda1 /mnt/sda1    

> sudo cp -rf /media/myusb/ubuntu-efi/EFI/ubuntu /mnt/sda1/EFI/

> sudo cp -rf /media/myusb/ubuntu-efi/EFI/BOOT /mnt/sda1/EFI/

Successfully Tested Scenarios

Scenario 1 

1. Create a virtual machine and install Ubuntu with VirtualBox, enabling EFI mode
- Partition 1: 500 MB (EFI system)
- Partition 2: 50 GB (FAT32 - empty)
- Partition 3: 200 GB (NTFS - empty)
- Partition 4: 40 GB (EXT4 - Ubuntu)
2. Reboot into Ubuntu Live through a virtual CD-ROM attached with the Ubuntu installation ISO file and choose Try Ubuntu
3. Open Disks application from the menu and use it to backup Partition 4 (Ubuntu system partition) to a disk image (*.img file) stored on Partition 3.
4. Restore the disk image file to Partition 2
5. Format and erase Partition 4
6. Optional: backup Partition 1 to a disk image stored on Partition 3
7. Close the virtual machine and start it again

Scenario 2

1. Boot into Recovery mode on MacBook Pro Late 2011
2. Create the following partitions:
- Partition 1: 70 GB (Mac OS Extended)
- Partition 2: 100 GB (exFAT)
- Partition 3: 90 GB (FAT 32)
- Partition 4: 200 GB (exFAT)
3. Install macOS High Sierra on Partition 1 
4. Install Ubuntu 20.04 on Partition 3 (formatted as ext4)
5. Boot into Ubuntu Live USB and choose Try Ubuntu
6. Open Disks application from the menu
7. Format Partition 4 as NTFS
8. Optional: resize Partition 3 to 20 GB (leaving 70 GB of free space)
9. Backup Partition 3 (Ubuntu) as a disk image (*.img file) and store it on Partition 4 
10. Format and erase Partition 3 (this can also be done in macOS)
11. Restore the disk image from Partition 4 to Partition 3
12. Reboot the machine

Setting environment variables on Ubuntu

Example

export JAVA_HOME=/usr/local/jdk-15.0.2

export PATH="$PATH:$JAVA_HOME/bin"

Without the export command, the variables are just shell variables; it means they aren't recognized by the sub processes or programs that start from the shell. 

Login shell vs non-login shell

A shell in Unix is a program that provides command line interface for OS and user interaction. The Terminal application is just an emulator or GUI for a shell.

Login shell - ssh is an example.

Non-login shell - the Terminal application by default starts a non-login shell but inherits the user environment variablbes loaded from the graphical login shell.

Session-wide environment variables

It affects only specific user.

The ~/.profile file

Each user has its own .profile file. It gets executed by the DisplayManager when the desktop session loads as well as by the login shell when one logs in from the textual console.

The ~/.profile file is not automatically executed by just restarting the Terminal application because it's not a login shell. For the file modification to take effect, logout the user account and login again.

System-wide environment variables

It affects the system as a whole (rather than just a specific user). 

The /etc/environment file

The downside is variables do not expand. In the example below, the PATH variable would end up containing only "/bin" because $PATH and $JAVA_HOME don't get replaced with their values.

export JAVA_HOME=/usr/local/jdk-15.0.2

export PATH="$PATH:$JAVA_HOME/bin"

The /etc/profile & /etc/profile.d/*.sh files

The /etc/profile is often used for setting system-wide environment variables but it is a configuration file so it's inappropriate to edit that file. The /etc/profile.d directory should be used instead. It (and any sh files inside) get executed whenever a bash login shell is entered (e.g. when logging in from the console or over ssh), as well as by the DisplayManager when the desktop session loads. 

For example, create the /etc/profile.d/myvars.sh file and set the variables as followings:

export JAVA_HOME=/usr/local/jdk-15.0.2

export PATH="$PATH:$JAVA_HOME/bin"

WiFi is not working on a fresh-install Ubuntu 20.04

I'm using Macbook Pro Late 2011 to install Ubuntu 20.04 on it. WiFi was working fine when trying Ubuntu from Live USB, but it wasn't after the installation. I couldn't find the WiFi adapter in Network settings.

First, when I opened Software & Updates > Additional Drivers, I saw:

Broadcom Inc. and subsidaries: BCM4331 802. 11a/b/g/n (AirPort Extreme)

The option Do not use the device  below it was checked and then I check another option to use the device and clicked Apply Changes but failed.

Second, I mounted the Ubuntu installation ISO file as a CD-ROM (using commands in Terminal) then opened Software & Updates again and selected Ubuntu Software tab. Under Installable from CD-ROM/DVD label, I checked Cdrom with Ubuntu 20.04 then repeat the first step but still no luck.

The solution below (that I copied from here) worked. 

1. Extract the Ubuntu installation ISO file (ubuntu-20.04.*.iso) to ~/Downloads folder then open Terminal and run:

> sudo chmod -R 777 ~/Downloads/ubuntu-20.04.*

2. Find the broadcom firmware on another machine:

- Download broadcom-wl-6.30.163.46.tar.bz2 (or later) from here or my backup.

- Extract it to ~/Downloads folder

3. Run the following commands in Terminal:

> cd ubuntu-20.04.*/

> sudo dpkg -i ./pool/main/b/b43-fwcutter/b43-fwcutter_019-4_amd64.deb

> cd ~/Downloads/broadcom-wl-6.30.163.46

> sudo b43-fwcutter -w /lib/firmware broadcom-wl-6.30.163.46.wl_apsta.o

 

> sync

> sudo modprobe -r b43 

> sudo modprobe b43 

4. Check the Network settings again and the WiFI icon should appear.