The issue manifests in our StopContextTimeoutTest running under Windows. In this tests we stop a container while it is receiving tens of thousands of parallel requests. So the process of stopping/removing takes a very long time, and sometimes the test framework's start.stop.timeout kicks in and deletes the contexts while the server is stopping.

Tomcat HostConfig.checkResources sleeps for 500ms in a synchronized method if a resource is not found. This sleep delays the stop of the container and can cause the errors seen in our StopContextTimeoutTest and reported previously in MODCLUSTER-782.

After some discussion with rhn-engineering-jclere he opened PR-641 that is still not merged either in the tomcat-10 or in the tomcat-9 branches.