Recently we tried to upgrade our jenkins master from jenkins-2.287.war to jenkins-2.321.war. We did the same jenkins upgrade and its plugins upgrade in one Mac host. I was successfully.

But in one CentOS-7 VM host, it failed with below error message.

jenkins.service - LSB: Jenkins Automation Server
  Loaded: loaded (/etc/rc.d/init.d/jenkins; bad; vendor preset: disabled)
  Active: failed (Result: timeout) since Wed 2022-01-12 02:30:49 PST; 33min ago
   Docs: man:systemd-sysv-generator(8)
 Process: 31106 ExecStop=/etc/rc.d/init.d/jenkins stop (code=exited, status=0/SUCCESS)
 Process: 32363 ExecStart=/etc/rc.d/init.d/jenkins start (code=killed, signal=TERM)
  Tasks: 264
  CGroup: /system.slice/jenkins.service
      ├─32370 runuser -s /bin/bash jenkins -c ulimit -S -c 0 >/dev/null 2>&1 ; /etc/alternatives/java -Djava.awt.headless=true -DJENKINS_HOME=/home/jenkin...
      ├─32371 bash -c ulimit -S -c 0 >/dev/null 2>&1 ; /etc/alternatives/java -Djava.awt.headless=true -DJENKINS_HOME=/home/jenkins -jar /usr/lib/jenkins/...
      └─32372 /etc/alternatives/java -Djava.awt.headless=true -DJENKINS_HOME=/home/jenkins -jar /usr/lib/jenkins/jenkins.war --logfile=/var/log/jenkins/je...Jan 12 02:25:49 jenkins-lnx.filemaker.com systemd[1]: Starting LSB: Jenkins Automation Server...
Jan 12 02:25:49 jenkins-lnx.filemaker.com runuser[32370]: pam_unix(runuser:session): session opened for user jenkins by (uid=0)
Jan 12 02:30:49 jenkins-lnx.filemaker.com systemd[1]: jenkins.service start operation timed out. Terminating.
Jan 12 02:30:49 jenkins-lnx.filemaker.com systemd[1]: Failed to start LSB: Jenkins Automation Server.
Jan 12 02:30:49 jenkins-lnx.filemaker.com systemd[1]: Unit jenkins.service entered failed state.

But we still could login into jenkins and ran jobs.

If we rolled back jenkins version to jenkins-2.311.war, 'sudo systemctl start jenkins' worked well.

Please let me know if you need more information to fix this issue.