Well, spent the morning again on this and finally found the problem, but I'm not sure where the problem is.
I had guess about the logging, not sure why, so I added "log4j-1.2.17.jar" to the classpath.
JBoss Logging using it instead of JDK14 logging.
Redeploys are now occurring correctly.
So, where should I report this? JBoss Logging project? Oracle's JDK issue tracker?