Can't see the second node whilst attempting to build a cluster

Hi, the messages you were seeing that you had to explicitly enable Security might have been showing up because you had settings in your elasticsearch.yml file. ES warned you that it can't do anything with those settings because Security wasn't automatically enabled for your Trial license.

If that was the case, you don't need to enable security, just take out the settings from your elasticsearch.yml that try to configure security features.

From there on, it looks like Kibana was failing to start up completely because it could not authenticate with Elasticsearch. That could have happened because no users were created in ES, or kibana.yml did not have the auth config lines (elasticsearch.username, elasticsearch.password) or it had the incorrect auth. Since it says missing authentication token I think that means you had no auth settings in your kibana.yml

Other than node.master: true in one node and true in another, is everything in the ES configs exactly the same? Since security is popping up as a trouble spot, you might have had different security settings in one of the configs.

Networking wise, the two hosts are able to communicate and both configs are near enough identical

How do you determine the network status? To verify what you say, you'd need to check:

curl https://elasticsearch:9200/_cluster/health

and look for:

  "number_of_nodes": 2

in the response. Invalid security settings will certainly prevent a node from joining a cluster, so check for that.

Hope that helps!

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