Kibana Service Fails when SSL Cert Enabled

It looks like you're on the right track, the error seems to indicate an issue opening the file. Kibana packages using systemd run as the user 'kibana' Can you make sure permissions on your certificates allow for read access to the file as either user or group kibana? If you chown kibana /etc/letsencrypt/live/api.domain.com/privkey.pem for example are you able to start the server?