Why is security setup so ridiculously awkward?

With each release of Elasticsearch, the security setup process gets more and more complex and less and less stable. Anytime the ES server is restarted, Kibana loses its ability to authenticate without generating a new token.

This setup process is absolute garbage and I wish you all would streamline it because this is piss poor behavior from a once great product.

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That is not how the service tokens work. Perhaps you could open a topic about it and we can try and work out why you are seeing that behaviour.