Is it safe to upgrade Ubuntu from 14.04 to 16.04.1 via do-release-upgrade, and how-to

Give it a shot and let us know how it goes!

well I upgraded our root server (no droplet) from 18.04.5 LTS to 20.04.1 LTS two weeks ago and discourse is running fine.
Just for the upgrade I had to manually change /etc/apt/sources.list and replace bonic by focal and ftp by http (ftp is deactived by default in 20).
But when I did the upgrade vom 16.04.6 LTS to 18.04.3 LTS beginning of the year I also had to change it manually from xenial to bionic since do-release-upgrade did run on error.
So this might only be a problem caused by my hoster Strato here in Germany.

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Thank You,
I have a Discourse Droplet on Digital Ocean and I’m wondering what’s the safest way to upgrade.

The safest way is to do a clean install on a new droplet and migrate the data. That way the old server keeps working while you configure and test the new one.

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