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I decided to do some additional tracking of last known working version of jenkins.war where --webroot parameter took effect.
I downloaded previous versions and ran test to see which last known version set webroot to defined: /var/cache/jenkins folder.
Last Version to allow --webroot option was: v 1.534
jenkins-1.534.war - Pass!
jenkins-1.535.war - Fail!
INFO: Extract jar:file:/usr/share/jenkins/jenkins-1.535.war!/ to /tmp/jetty-0.0.0.0-8080-jenkins-1.535.war-
any/webappSo it appears this change was implemented in v.1.535 - 1.540 (current). I ran several test on 1.537, 1.538, 1.539 and same results.