Start EAP Define security realm needed by the web application /subsystem=security/security-domain=web-tests:add(cache-type=default) /subsystem=security/security-domain=web-tests/authentication=classic:add(login-modules=[{"code"=>"UsersRoles", "flag"=>"required"}]) {allow-resource-service-restart=true} Define Single Sign On ( /subsystem=undertow/server=default-server/host=default-host/setting=single-sign-on:add() ) Deploy the same web application https://github.com/kwart/secured-webapp-template/releases/download/single-jsp-app/secured-webapp.war under two names (secured-webapp.war and secured-webapp2.war) Go to fist web app via your web browser and log in there ( http://localhost:8080/secured-webapp/user/ , credentials are user:user) Go to second web app via your web browser ( http://localhost:8080/secured-webapp2/user/ ) You should be automatically logged thanks to enabled SSO, but you aren't and you are required to input credentials again.