I get the same error with a different stack trace on 1.532.1 on Windows Server 2008 R2:

Dec 9, 2013 5:33:04 PM winstone.Logger logInternal
SEVERE: Error while serving http://vmw4360.wdf.sap.corp:50000/administrativeMonitor/OldData/discard
java.lang.reflect.InvocationTargetException
at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
at java.lang.reflect.Method.invoke(Method.java:597)
at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:297)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:160)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:95)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:111)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:685)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:799)
at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:239)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:685)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:799)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:587)
at org.kohsuke.stapler.Stapler.service(Stapler.java:218)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:45)
at winstone.ServletConfiguration.execute(ServletConfiguration.java:248)
at winstone.RequestDispatcher.forward(RequestDispatcher.java:333)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:376)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:96)
at net.bull.javamelody.MonitoringFilter.doFilter(MonitoringFilter.java:203)
at net.bull.javamelody.MonitoringFilter.doFilter(MonitoringFilter.java:181)
at net.bull.javamelody.PluginMonitoringFilter.doFilter(PluginMonitoringFilter.java:86)
at org.jvnet.hudson.plugins.monitoring.HudsonMonitoringFilter.doFilter(HudsonMonitoringFilter.java:84)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:99)
at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:58)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:99)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:88)
at winstone.FilterConfiguration.execute(FilterConfiguration.java:194)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:366)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:48)
at winstone.FilterConfiguration.execute(FilterConfiguration.java:194)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:366)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)
at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:51)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at jenkins.security.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:117)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.providers.anonymous.AnonymousProcessingFilter.doFilter(AnonymousProcessingFilter.java:125)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.ui.rememberme.RememberMeProcessingFilter.doFilter(RememberMeProcessingFilter.java:142)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.ui.AbstractProcessingFilter.doFilter(AbstractProcessingFilter.java:271)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.ui.basicauth.BasicProcessingFilter.doFilter(BasicProcessingFilter.java:174)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at jenkins.security.ApiTokenFilter.doFilter(ApiTokenFilter.java:64)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.context.HttpSessionContextIntegrationFilter.doFilter(HttpSessionContextIntegrationFilter.java:249)
at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:67)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)
at winstone.FilterConfiguration.execute(FilterConfiguration.java:194)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:366)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:46)
at winstone.FilterConfiguration.execute(FilterConfiguration.java:194)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:366)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:81)
at winstone.FilterConfiguration.execute(FilterConfiguration.java:194)
at winstone.RequestDispatcher.doFilter(RequestDispatcher.java:366)
at winstone.RequestDispatcher.forward(RequestDispatcher.java:331)
at winstone.RequestHandlerThread.processRequest(RequestHandlerThread.java:227)
at winstone.RequestHandlerThread.run(RequestHandlerThread.java:150)
at java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:441)
at java.util.concurrent.FutureTask$Sync.innerRun(FutureTask.java:303)
at java.util.concurrent.FutureTask.run(FutureTask.java:138)
at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)
at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(ThreadPoolExecutor.java:886)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:908)
at java.lang.Thread.run(Thread.java:662)
Caused by: java.util.ConcurrentModificationException
at java.util.HashMap$HashIterator.remove(HashMap.java:811)
at hudson.diagnosis.OldDataMonitor.doDiscard(OldDataMonitor.java:276)
... 73 more

This is related to an issue I put on the user list (https://groups.google.com/forum/#!topic/jenkinsci-users/ZK1J6R2ej4I) where disabling the disk-usage plugin resulted in a huge amount of old data - thousands of rows of "CannotResolveClassException: hudson.plugins.disk_usage.BuildDiskUsageAction" - clicking the Discard Old Data button results in the stack trace about.

Some further information on this after experimentation: I had some success deleting the vast amount of old data created by the disk-usage plugin. After stopping all jobs, I was able to delete some of the old data before the CME was thrown. I was able to go back to the Manage Old Data screen and it listed more old data. Again, I deleted it. Sometimes this would throw a CME, sometimes it appeared to work. After a few minutes, if I go back to Manage Old Data, there would be more entries to delete. My guess is that the OldDataMonitor continuously scans for old data and - when found - holds onto it so it can be displayed in the Manage Old Data screen. This seems to be a bad idea because of https://issues.jenkins-ci.org/browse/JENKINS-19544. However, after about a dozen "Discard Old Data" runs, my old data seems to be at a small enough size that I no longer get nightly OOM errors.

Old Data Monitor was substantially changed in 1.557 for JENKINS-19544. Closing this speculatively as the similar JENKINS-22261 was also resolved.

Reopen or file a new issue when this still occurs on 1.557 or newer.

This issue is happening in Jenkins 1.565 after migrating from Hudson.

Here is my stack:
javax.servlet.ServletException: java.util.ConcurrentModificationException
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:778)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)
at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:248)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:631)
at org.kohsuke.stapler.Stapler.service(Stapler.java:225)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:848)
at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:686)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1494)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:96)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:88)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:48)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:46)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:81)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1474)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:499)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:137)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:533)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:231)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1086)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:428)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:193)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1020)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:135)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:116)
at org.eclipse.jetty.server.Server.handle(Server.java:370)
at org.eclipse.jetty.server.AbstractHttpConnection.handleRequest(AbstractHttpConnection.java:489)
at org.eclipse.jetty.server.AbstractHttpConnection.content(AbstractHttpConnection.java:960)
at org.eclipse.jetty.server.AbstractHttpConnection$RequestHandler.content(AbstractHttpConnection.java:1021)
at org.eclipse.jetty.http.HttpParser.parseNext(HttpParser.java:865)
at org.eclipse.jetty.http.HttpParser.parseAvailable(HttpParser.java:240)
at org.eclipse.jetty.server.AsyncHttpConnection.handle(AsyncHttpConnection.java:82)
at org.eclipse.jetty.io.nio.SelectChannelEndPoint.handle(SelectChannelEndPoint.java:668)
at org.eclipse.jetty.io.nio.SelectChannelEndPoint$1.run(SelectChannelEndPoint.java:52)
at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)
at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(Unknown Source)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
at java.lang.Thread.run(Unknown Source)
Caused by: java.util.ConcurrentModificationException
at java.util.HashMap$HashIterator.nextEntry(Unknown Source)
at java.util.HashMap$EntryIterator.next(Unknown Source)
at java.util.HashMap$EntryIterator.next(Unknown Source)
at hudson.diagnosis.OldDataMonitor.doDiscard(OldDataMonitor.java:297)
at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)
at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)
at java.lang.reflect.Method.invoke(Unknown Source)
at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:298)
at org.kohsuke.stapler.interceptor.RequirePOST$Processor.invoke(RequirePOST.java:46)
at org.kohsuke.stapler.Function$InterceptedFunction.invoke(Function.java:399)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:161)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:96)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:120)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)
... 46 more

Any assistance would be appreciated.

Related code changed by fix of JENKINS-30139.