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.
>

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