Best Jenkins Upgrade Path for 2.73.1 to latest

Hello Jenkins Community,

I hope this message finds you well. I am currently managing a Jenkins instance running version 2.73.1, and I’m interested in upgrading it to the latest version. I wanted to reach out to the community to seek advice and recommendations on the best upgrade path for this process.

Here are some specific questions I have in mind:

  1. What is the recommended upgrade path from Jenkins version 2.73.1 to the latest version?
  2. Are there any specific LTS versions I should consider during the incremental upgrade process?
  3. Have there been any major changes or considerations in the recent Jenkins releases that I should be aware of during the upgrade?

I would greatly appreciate insights, best practices, and any experiences you can share regarding upgrading Jenkins to the latest version. Additionally, if there are specific steps, tips, or precautions that I should keep in mind during this process, I would be very grateful for your guidance.

Thank you in advance for your time and assistance. Your expertise will be invaluable in ensuring a smooth and successful Jenkins upgrade.

There is a lot to consider when upgrading, I wrote a blog post a few months ago with lessons learned from my own experience, along with links and resources that I found helpful: Back of the Napkin Guide to Updating Jenkins, for the uninitiated

You can go version by version; but you can also make jumps by multiple versions. I HIGHLY recommend you read thru the change logs for every version; and keep a matrix of changes to test. You’ll likely want to jump from 2.73.1 to 2.426.x over multiple steps.

The other option may also be to just start with a fresh install at your target version, add in required plugins; and start there. I don’t have experience on copying over previous workspaces, and jobs; if that’s even possible from that far back? Someone else will chime in there.

You will absolutely have to do your upgrade in multiple steps. I started from a much later version and needed to do the same. Your biggest challenge today is the fact that the update server only provides plugins for the previous year so many of your plugins aren’t even going to be able to update until you get into the 300s.