With a long running windows/msbuild job running on master, another change is submitted, and the next job is queued up. If the current running job is cancelled, Jenkins immediately switches to running the next job. The job is configured to delete changed files and check out new. It looks like the previous job still has files open when jenkins starts to delete, which results in an IOException (Below)

Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\MyProjectItemServiceInstaller.sln.cache
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\PSWixLib\bin
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\PSWixLib\obj
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CommonLibWixLib\bin
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CommonLibWixLib\obj
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CRServiceInstaller\bin
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CRServiceInstaller\obj
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CRServiceWixLib\bin
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\MyProjectItemServiceInstaller\CRServiceWixLib\obj
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\NetSetup\NetSetup.sln.cache
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\NetSetup\Release
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\genericproject.sln.cache
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\hlp
Deleting F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\obj
ERROR: Failed to update https://svn.example.com/svn/my_service/trunk
org.tmatesoft.svn.core.SVNException: svn: Unable to delete F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\obj\Release\BuildLog.htm
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl$1.handleStatus(UpdateWithCleanUpdater.java:78)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.sendUnversionedStatus(SVNStatusEditor.java:358)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:208)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.handleDirEntry(SVNStatusEditor.java:318)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.handleDirEntry(SVNStatusEditor.java:318)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.closeEdit(SVNStatusEditor.java:114)
at org.tmatesoft.svn.core.wc.SVNStatusClient.doStatus(SVNStatusClient.java:380)
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl.preUpdate(UpdateWithCleanUpdater.java:83)
at hudson.scm.subversion.UpdateUpdater$TaskImpl.perform(UpdateUpdater.java:133)
at hudson.scm.subversion.WorkspaceUpdater$UpdateTask.delegateTo(WorkspaceUpdater.java:136)
at hudson.scm.SubversionSCM$CheckOutTask.perform(SubversionSCM.java:787)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:768)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:752)
at hudson.FilePath.act(FilePath.java:783)
at hudson.FilePath.act(FilePath.java:765)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:742)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:686)
at hudson.model.AbstractProject.checkout(AbstractProject.java:1195)
at hudson.model.AbstractBuild$AbstractRunner.checkout(AbstractBuild.java:568)
at hudson.model.AbstractBuild$AbstractRunner.run(AbstractBuild.java:457)
at hudson.model.Run.run(Run.java:1404)
at hudson.model.FreeStyleBuild.run(FreeStyleBuild.java:47)
at hudson.model.ResourceController.execute(ResourceController.java:88)
at hudson.model.Executor.run(Executor.java:238)
Caused by: org.tmatesoft.svn.core.SVNErrorMessage: svn: Unable to delete F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\obj\Release\BuildLog.htm
at org.tmatesoft.svn.core.SVNErrorMessage.create(SVNErrorMessage.java:101)
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl$1.handleStatus(UpdateWithCleanUpdater.java:78)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.sendUnversionedStatus(SVNStatusEditor.java:358)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:208)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.handleDirEntry(SVNStatusEditor.java:318)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.handleDirEntry(SVNStatusEditor.java:318)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.closeEdit(SVNStatusEditor.java:114)
at org.tmatesoft.svn.core.wc.SVNStatusClient.doStatus(SVNStatusClient.java:380)
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl.preUpdate(UpdateWithCleanUpdater.java:66)
at hudson.scm.subversion.UpdateUpdater$TaskImpl.perform(UpdateUpdater.java:133)
at hudson.scm.subversion.WorkspaceUpdater$UpdateTask.delegateTo(WorkspaceUpdater.java:136)
at hudson.scm.SubversionSCM$CheckOutTask.perform(SubversionSCM.java:787)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:768)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:752)
at hudson.FilePath.act(FilePath.java:783)
at hudson.FilePath.act(FilePath.java:765)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:742)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:684)
at hudson.model.AbstractProject.checkout(AbstractProject.java:1195)
at hudson.model.AbstractBuild$AbstractRunner.checkout(AbstractBuild.java:568)
at hudson.model.AbstractBuild$AbstractRunner.run(AbstractBuild.java:457)
at hudson.model.Run.run(Run.java:1404)
at hudson.model.FreeStyleBuild.run(FreeStyleBuild.java:46)
... 2 more
Caused by: java.io.IOException: Unable to delete F:\jenkins\jobs\MyProject\workspace\my_service\genericproject\Source\obj\Release\BuildLog.htm
at hudson.Util.deleteFile(Util.java:266)
at hudson.Util.deleteRecursive(Util.java:316)
at hudson.Util.deleteContentsRecursive(Util.java:227)
at hudson.Util.deleteRecursive(Util.java:307)
at hudson.Util.deleteContentsRecursive(Util.java:227)
at hudson.Util.deleteRecursive(Util.java:307)
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl$1.handleStatus(UpdateWithCleanUpdater.java:74)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:208)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.getDirStatus(SVNStatusEditor.java:253)
at org.tmatesoft.svn.core.internal.wc.SVNStatusEditor.closeEdit(SVNStatusEditor.java:114)
at org.tmatesoft.svn.core.wc.SVNStatusClient.doStatus(SVNStatusClient.java:380)
at hudson.scm.subversion.UpdateWithCleanUpdater$TaskImpl.preUpdate(UpdateWithCleanUpdater.java:83)
at hudson.scm.subversion.UpdateUpdater$TaskImpl.perform(UpdateUpdater.java:133)
at hudson.scm.subversion.WorkspaceUpdater$UpdateTask.delegateTo(WorkspaceUpdater.java:136)
at hudson.scm.SubversionSCM$CheckOutTask.perform(SubversionSCM.java:787)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:768)
at hudson.scm.SubversionSCM$CheckOutTask.invoke(SubversionSCM.java:752)
at hudson.FilePath.act(FilePath.java:783)
at hudson.FilePath.act(FilePath.java:765)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:742)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:686)
at hudson.model.AbstractProject.checkout(AbstractProject.java:1195)
at hudson.model.AbstractBuild$AbstractRunner.checkout(AbstractBuild.java:568)
at hudson.model.AbstractBuild$AbstractRunner.run(AbstractBuild.java:457)
at hudson.model.Run.run(Run.java:1404)
at hudson.model.FreeStyleBuild.run(FreeStyleBuild.java:47)
... 2 more
FATAL: null
java.lang.NullPointerException
at java.util.ArrayList.addAll(ArrayList.java:472)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:742)
at hudson.scm.SubversionSCM.checkout(SubversionSCM.java:684)
at hudson.model.AbstractProject.checkout(AbstractProject.java:1195)
at hudson.model.AbstractBuild$AbstractRunner.checkout(AbstractBuild.java:568)
at hudson.model.AbstractBuild$AbstractRunner.run(AbstractBuild.java:457)
at hudson.model.Run.run(Run.java:1404)
at hudson.model.FreeStyleBuild.run(FreeStyleBuild.java:46)
at hudson.model.ResourceController.execute(ResourceController.java:88)
at hudson.model.Executor.run(Executor.java:238)