I notice that cert-manager recommends upgrading versions in some specific order. So for users who are running 1.12.9 as currently installed by kops, they should first upgrade to v1.17.4, then to v1.18.4, then to v1.19.2. I wonder if this change requires some care here to avoid breaking things.

I am not sure what consequences there would be with skipping versions, though. Maybe it's actually fine. I can't say for sure.

https://cert-manager.io/docs/releases/upgrading/upgrading-1.12
https://cert-manager.io/docs/releases/upgrading/upgrading-1.17-1.18
https://cert-manager.io/docs/releases/upgrading/upgrading-1.18-1.19
https://cert-manager.io/docs/installation/upgrade/
https://cert-manager.io/docs/installation/kubectl/#verify

Maybe we need to add some more control over cert-manager versions into kops somehow.

Currently you can change the "image" for cert-manager in the kops config, but to upgrade you also need to update the Custom Resource Definitions to match or you might run into problems. They also seem to have switched around the deployment manifests a little bit over time.

cert-manager: update to new version #17798

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