News! It's 2019!
Usually the uneven years are "boring". There is no big football tournament in summer. That's probably the reason why Canonical decided to use uneven years as EOL year for their long term support (LTS) versions.
Ubuntu 14.04 (Trusty Tahr) was released in April 2014 (hence 14.04) and came with a 5 year LTS "patching warranty". That's 2019. Oh no, that's now!
So it's time to upgrade the still running (and damn stable! pre-systemd... ;P) 14.04 machines.
For the sake of documentation, I noted down my double-release-upgrade steps from 14.04 -> 16.04 -> 18.04.
0. Before you even begin, make sure you have a backup. Create a snapshot of your VM, of your LXC LV's, dd your hard drive or whatever you're using.
1. Run apt-get update and apt-get dist-upgrade on existing version to get the latest updates.
# apt-get update && apt-get dist-upgrade
Note: I'd even reboot the machine afterwards, to make sure the latest Kernel is running.
2. Copy existing apt source list file /etc/apt/sources.list
# cp -p /etc/apt/sources.list{,.trusty}
3. Disable special sources in /etc/apt/sources.list.d/ directory -> rename files to end with .disabled or similar
# for file in $(ls /etc/apt/sources.list.d/*.list); do mv ${file} ${file}.disabled; done
4. Create the new /etc/apt/sources.list for 16.04 (xenial):
deb http://ch.archive.ubuntu.com/ubuntu/ xenial main restricted universe multiverse
deb http://ch.archive.ubuntu.com/ubuntu/ xenial-updates main restricted universe multiverse
deb http://security.ubuntu.com/ubuntu xenial-security main restricted universe multiverse
Note: Obviously you should use your own local mirror or country.
5. Run apt-get update and apt-get dist-upgrade. If apt asks to overwrite config files, usually chose "Y" to get the new config file from the updated package, unless you're sure that you require the current config file.
# apt-get update && apt-get dist-upgrade
6. If no errors occurred during dist-upgrade, reboot
# reboot
7. Verify system/applications work
8. Copy existing apt source list file /etc/apt/sources.list -> /etc/apt/sources.list.xenial
# cp -p /etc/apt/sources.list{,.xenial}
9. Create the new /etc/apt/sources.list for 18.04 (bionic):
deb http://ch.archive.ubuntu.com/ubuntu/ bionic main restricted universe multiverse
deb http://ch.archive.ubuntu.com/ubuntu/ bionic-updates main restricted universe multiverse
deb http://security.ubuntu.com/ubuntu bionic-security main restricted universe multiverse
10. Run apt-get update and apt-get dist-upgrade. If apt asks to overwrite config files, usually chose "Y" to get the new config file from the updated package, unless you're sure that we require the current config file (in my case that was only nrpe.cfg).
# apt-get update && apt-get dist-upgrade
11. If no errors occurred during dist-upgrade, reboot
# reboot
12. Verify system/applications work
13. Enable additional apt sources in /etc/apt/sources.list.d (adjust them to match the new distribution version). Maybe this requires manual research to see if these additional/third party repos even support the new distribution version.
Hopefully these steps worked as fine for you as they did for me. It always depends on the applications you're running on the Ubuntu machine of course.
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