This readily manifests in GH Actions testing, for example:
 https://github.com/shipilev/jdk/runs/1748754939

Reproducible locally with:

$ CONF=linux-x86-server-fastdebug make images run-test TEST=sun/misc/JarIndex/metaInfFilenames/Basic.java

----------------------------------
Running test looking for /META-INF/unknown.mf
Server: received request for /a.jar
HttpServer: aDotJar=1, bDotJar=0, cDotJar=0
STDERR:
java.lang.InternalError: java.io.IOException: Invalid argument
at java.base/sun.nio.ch.EPollSelectorImpl.wakeup(EPollSelectorImpl.java:253)
at jdk.httpserver/sun.net.httpserver.ServerImpl.stop(ServerImpl.java:192)
at jdk.httpserver/sun.net.httpserver.HttpServerImpl.stop(HttpServerImpl.java:70)
at Basic$JarHttpServer.stop(Basic.java:350)
at Basic.main(Basic.java:118)
at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:78)
at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
at java.base/java.lang.reflect.Method.invoke(Method.java:566)
at com.sun.javatest.regtest.agent.MainWrapper$MainThread.run(MainWrapper.java:127)
at java.base/java.lang.Thread.run(Thread.java:831)
Caused by: java.io.IOException: Invalid argument
at java.base/sun.nio.ch.EventFD.set0(Native Method)
at java.base/sun.nio.ch.EventFD.set(EventFD.java:48)
at java.base/sun.nio.ch.EPollSelectorImpl.wakeup(EPollSelectorImpl.java:251)
... 10 more