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I'm looking for a way to automate the process. Has anyone got any ideas?

Currently relies on a fix to the appengine go SDK though: https://github.com/golang/appengine/pull/82

Wait so does this work?

Should do if you manually patch your local SDK.

If you have a Kubernetes cluster you can use https://github.com/PalmStoneGames/kube-cert-manager. Certbot (https://certbot.eff.org/) also has several configurations.