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When you install Wildfly as a service on Windows there are some logging parameters that set up separate logs for stdout, stderr, etc, in the service.bat file. I am not sure whether those logs were being written to properly as there does't seem to be a way to rotate them and they became too large. I removed the params for those from service.bat and now they are not being created, however the original logging problem still occurs. I can now reproduce this behavior on second system using the <periodic-rotating-file-handler> as set up in the default standalone.xml provided in the distro.