Is there a way to ease installing fleet server to a elasticsearch server secured by self-signed certificate

[blaker (Blake Rouse)]

Read the discussion here, it describes how the output settings must be configured in the Fleet settings flyout in Kibana.

7.14 - Windows agent deployed with Fleet, but not sending data

The issue is that using --insecure only allow Elastic Agent to communicate with Fleet Server insecurely. It still takes the settings from the policy to communicate with Elasticsearch. You need to modify the output settings inside the Fleet UI in Kibana. You will want to add the following in the Elasticsearch output configuration (YAML) block: ssl.verification_mode: none