Here’s my journey in the upgrade, it took around 10 hours. Thanks @rlkoshak with the overview above which helped!
I needed/wanted to upgrade Pi OS from Buster to Bullseye
sudo apt-mark hold openhab
sudo apt-mark hold openhab-addons
sudo apt-mark hold speedtest-cli
sudo apt-mark hold python3
sudo apt-mark hold openjdk-11-jre-headless:armhf
Show package status on Linux → validate the HOLD status on the above
dpkg --get-selections | less
https://jamesjdavis.medium.com/how-to-update-raspberry-pi-just-follow-these-easy-steps-ac507cf70238
sudo apt update
sudo apt dist-upgrade
sudo apt clean
sudo reboot
sudo nano /etc/apt/sources.list
Change buster to bullseye on first line
sudo apt update
https://unix.stackexchange.com/questions/592657/full-upgrade-to-debian-testing-fails-due-to-libc6-dev-breaks-libgcc-8-dev
sudo apt install gcc-8-base ← this resolves an error before upgrading
sudo apt dist-upgrade ← this will take a lot of time with default prompts
sudo apt autoclean
sudo reboot
Reinstall SAMBA if you use it
Upgrade Putty on your clients to latest vesion (0.79), older version won’t connect to Bullseye
Removed DHCP from Bullseye since I have a static IP and didn’t want the 169.x.x.x IP showing up
https://www.openhab.org/download/
curl -fsSL "https://openhab.jfrog.io/artifactory/api/gpg/key/public" | gpg --dearmor > openhab.gpg
sudo mkdir /usr/share/keyrings
sudo mv openhab.gpg /usr/share/keyrings
sudo chmod u=rw,g=r,o=r /usr/share/keyrings/openhab.gpg
OH 3.x should continue to run as normal with Bullseye installed now
** Make a SSD copy before proceeding to upgrade OH for a disaster backup scenario
Make sure OH is stopped before proceeding.
apt-get install openhab
sudo /bin/systemctl start openhab.service
Make sure OH is stopped before proceeding.
apt-get install openhab-addons
My upgrade took me from OH 3.4.4 to 4.0.4
Start OH
→ lots of “Could not resolve modules”
Stop OH
Removed these bindings in Addon’s due to resolutions never happening, need to upgrade them to 4.0.x versions once up and running via GUI
org.smarthomej.binding.androiddebugbridge
org.smarthomej.commons
org.openhab.io.hueemulation
org.smarthomej.binding.amazonechocontrol
Removed everything from /cache and /tmp
Start OH
Downloaded from Market Place:
org.smarthomej.binding.amazonechocontrol (beta)
org.smarthomej.binding.androiddebugbridge
Downloaded from jFrog, HUE Emulation, couldn’t find where to install/activate this via the GUI anywhere.
Stop OH
Reboot Pi