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I have a number of kubernetes clusters running on version 1.8 for kubeadm, kubectl, kubelet and associated containers.

I need to make a plan to get these clusters upgraded to 1.14. I see that the official recommendation is to go one version at a time, at least for 1.10 to 1.14 (https://kubernetes.io/docs/reference/setup-tools/kubeadm/kubeadm-upgrade/). Is that really necessary?

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Yes. It is always a good idea to follow the official recommendation. Personally, I have upgraded while skipping one or two minor versions with no repercussions, but you should understand this is a gamble and have a good backup to roll back to if the worst should happen.

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I would say it depend based on required, if anyone of the requirement is needed by your environment defiantly you should upgrade https://kubernetes.io/blog/2019/03/25/kubernetes-1-14-release-announcement/

Choice of upgrade depends on newly add features/platform dependancy/bug fixes/security etc.

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