Hi,
you ran into a Bootable JAR bug. I managed to reproduce a similar issue but with a different error message. The bug is that the security providers are not registered before elytron is initialized (something that is done in pure WildFly).
This explains why it works when you do it once the server is
started.
I logged: https://issues.redhat.com/browse/WFCORE-6270
You could try the fix by rebuilding this PR branch: https://github.com/wildfly/wildfly-core/pull/5418 and rebuild wildfly 28 SNAPSHOT (https://github.com/wildfly/wildfly) with -Dversion.org.wildfly.core=20.0.0.Beta8-SNAPSHOT
Thank-you.
JF
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