Hi @LutraMan,
Did you succeed bootstrapping your cluster? I have a very similar issue since my readinessProbe keeps receiving a 500 error because of “Opendistro security not initialized”.
I don’t even use tls over http, only transport tls, but the security plugins seems to require security to be fully initialized (on a working cluster) prior to answer with 200 OK to any api call.
Cheers