On Windows Jenkins has to restart service that is hosting it. What you are describing will happen when this service executes under account that does not have enough privileges to restart the service.
Check Jenkins log files (jenkins.err.log). You will probably see something like this: 29.3.2011 11:59:32 hudson.model.Hudson$18 run WARNING: Failed to restart Hudson java.io.IOException: Restarting a service [service] $ D:\jenkins\service\jenkins.exe restart WMI.WmiException: AccessDenied at WMI.WmiRoot.BaseHandler.CheckError(ManagementBaseObject result) at WMI.WmiRoot.InstanceHandler.Invoke(Object proxy, MethodInfo method, Object[] args) at WMI.Win32ServiceProxy.StopService() at winsw.WrapperService.Run(String[] _args) at winsw.WrapperService.Main(String[] args) at hudson.lifecycle.WindowsServiceLifecycle.restart(WindowsServiceLifecycle.java:131) at hudson.model.Hudson$18.run(Hudson.java:3074) Simple fix is to include Jenkins account under which Jenkins executes in local Administrators group and restart service. But proper solution is to give Jenkins account just enough privileges to restart Jenkins service (http://serverfault.com/questions/187302/how-do-i-grant-start-stop-restart-permissions-on-a-service-to-an-arbitrary-user). You can test your configuration with Safe Restart Plugin (https://wiki.jenkins-ci.org/display/JENKINS/SafeRestart+Plugin). If this plugin is able to restart Jenkins, so should upgrade procedure. On Sunday, April 15, 2012 2:38:03 PM UTC+2, Ido Ran wrote: > > Hi, > After every upgrade I do from inside Jenkins it get stuck with "Please > wait while Jenkins is restarting" message. > I have to manually connect to the server stop and start it. > I use Windows 7 Pro to run Jenkins (because I build .NET application). I > run Jenkins as Windows Service. >