When using NIO connectors, it appears that the contextDestroyed method is not invoked. Tested on Apache Tomcat 9.0.104 and 10.1.44.

Configuration (server.xml – Connector tag):

• Using

  protocol="org.apache.coyote.http11.Http11Nio2Protocol"
  protocol="org.apache.coyote.http11.Http11Nio1Protocol"
  

  contextDestroyed is not called.

• Using

  protocol="org.apache.coyote.http11.Http11AprProtocol"
  

  contextDestroyed is called as expected.