I needed to dust off my trusty Raspberry Pi 2 for a new project, only to discover its Raspbian version was ancient history. With no SD-card reader in sight, I took the road less traveled: a manual upgrade adventure.

I’ve set out on a quest to build myself a homelab, with some network infrastructure. As VPN gateway I decided to use my Raspberry PI 2, with 1GB of RAM and a ARMv7 1200Mhz processor.

I booted up the Raspberry, and used the recovery mode to reset the OS to its original, which was Raspbian Jessie. With Jessie officially retired and brimming with potential security risks, upgrading to the shiny new Raspbian Bookworm became my quest.

I didn’t have an SD-card reader, so I couldn’t just flash a new image to the SD-card. No problem! We can just manually upgrade.

Since Raspbian installs with a GUI, lets get rid of that first. With Ctrl+Alt+1 we can switch to a terminal. Login with pi and password raspberry. You should change this later ;)

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# Remove GUI packages to free up space and simplify the system.
sudo apt purge --auto-remove \
raspberrypi-ui-mods lxpanel lxappearance openbox lightdm xserver* \
libreoffice* gvfs* desktop-base pix* gnome* gpicview xarchiver \
chromium* x11-xserver-util xserver-xorg libx11-* wolfram-engine xarchiver \
xfont* desktop-base openjdk-11-jdk libgtk2* libgtk* imagemagick* \
gnome-icon-theme adwaita-icon-theme qt-* qt5* xpdf* *wayland*

⚠️️ This command aggressively removes GUI-related packages and dependencies. Double-check the list to ensure you’re not removing something critical for your setup.

Now for the upgrading process, upgrading directly to the newest version is not recommended because of the huge amount of changes in dependencies.

Since we’re working with Jessie we can’t use the configured repository, since it’s no longer available.

→ Remove all other lines, and add this one to /etc/apt/sources.list:

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deb http://legacy.raspbian.org/raspbian/ jessie main contrib non-free rpi

→ Run the following commands to update all the Jessie packages:

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sudo apt update
sudo apt upgrade -y
sudo apt dist-upgrade -y
sudo apt autoremove -y

To Stretch

→ Now we can upgrade to Stretch. Change /etc/apt/sources.list to this line:

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deb http://legacy.raspbian.org/raspbian/ stretch main contrib non-free rpi

→ Replace jessie with stretch in the /etc/apt/sources.list.d/*.list files, and upgrade away:

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sudo sed -i 's/jessie/stretch/g' /etc/apt/sources.list.d/*.list
sudo apt update
sudo apt upgrade -y
sudo apt dist-upgrade -y
sudo apt autoremove -y

To Buster

→ Repeat the same to upgrade to Buster; in /etc/apt/sources.list:

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deb http://legacy.raspbian.org/raspbian/ buster main contrib non-free rpi

→ Then run:

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sudo sed -i 's/stretch/buster/g' /etc/apt/sources.list.d/*.list
sudo apt update
sudo apt upgrade -y
sudo apt dist-upgrade -y
sudo apt autoremove -y

To Bullseye

→ Again, repeat the same to upgrade to Bullseye; in /etc/apt/sources.list:

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deb http://raspbian.raspberrypi.org/raspbian/ bullseye main contrib non-free rpi

→ Then run:

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sudo sed -i 's/buster/bullseye/g' /etc/apt/sources.list.d/*.list

To upgrade to Bullseye, we manually have to remove the ui repo from the *.list files, since it’s not available anymore.

→ Edit every file in /etc/apt/sources.list.d/ and remove the ui string.

→ Now run the following, and pay attention to installing gcc-8-base:

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sudo apt update
sudo apt upgrade -y
sudo apt install gcc-8-base
sudo apt dist-upgrade -y
sudo apt autoremove -y

To Bookworm!

And lastly, we can upgrade to Bookworm. In /etc/apt/sources.list:

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deb http://raspbian.raspberrypi.org/raspbian/ bookworm main contrib non-free rpi

→ Now for the last time :)

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sudo sed -i 's/bullseye/bookworm/g' /etc/apt/sources.list.d/*.list
sudo apt update
sudo apt upgrade -y
sudo apt dist-upgrade -y
sudo apt autoremove -y
sudo reboot

And there you have it! A Raspberry Pi 2, manually upgraded to the latest version of Raspbian. Verify this by running cat /etc/os-release, and you should see:

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PRETTY_NAME="Raspbian GNU/Linux 12 (bookworm)"