I have this problem with Hudson 1.351 and I can provide a stacktrace. The problem is not new though, I have had it for months now.
I dont have an 404, but an 500 error but I end up having the same situation as shown in the screenshot attached.
19.03.2010 15:11:00 org.apache.catalina.core.ApplicationContext log
SEVERE: Error while serving http://xtcommon3host:7800/ibuild/nocacheImages/48x48/blue.gif
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:169)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:101)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:54)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:74)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:30)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:519)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:435)
at org.kohsuke.stapler.Stapler.service(Stapler.java:123)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:717)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:290)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:94)
at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:51)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:97)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:86)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:47)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
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 org.acegisecurity.ui.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:166)
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 hudson.security.BasicAuthenticationFilter.doFilter(BasicAuthenticationFilter.java:113)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:233)
at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:191)
at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:433)
at at.oenb.common.security.web.TomcatSpnegoValve.continueWithChain(TomcatSpnegoValve.java:881)
at at.oenb.common.security.web.TomcatSpnegoValve.invoke(TomcatSpnegoValve.java:508)
at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:128)
at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:102)
at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:567)
at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109)
at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:293)
at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:849)
at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:583)
at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:454)
at java.lang.Thread.run(Thread.java:619)
Caused by: java.lang.IllegalStateException
at org.apache.catalina.connector.ResponseFacade.sendError(ResponseFacade.java:421)
at javax.servlet.http.HttpServletResponseWrapper.sendError(HttpServletResponseWrapper.java:118)
at hudson.model.Hudson.doNocacheImages(Hudson.java:2791)
... 51 more
19.03.2010 15:11:00 org.apache.catalina.core.StandardWrapperValve invoke
SEVERE: Servlet.service() for servlet Stapler threw exception
java.lang.IllegalStateException
at org.apache.catalina.connector.ResponseFacade.sendError(ResponseFacade.java:421)
at javax.servlet.http.HttpServletResponseWrapper.sendError(HttpServletResponseWrapper.java:118)
at hudson.model.Hudson.doNocacheImages(Hudson.java:2791)
at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
at java.lang.reflect.Method.invoke(Method.java:597)
at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:169)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:101)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:54)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:74)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:30)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:519)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:435)
at org.kohsuke.stapler.Stapler.service(Stapler.java:123)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:717)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:290)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:94)
at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:51)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:97)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:86)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:47)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
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 org.acegisecurity.ui.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:166)
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 hudson.security.BasicAuthenticationFilter.doFilter(BasicAuthenticationFilter.java:113)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:233)
at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:191)
at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:433)
at at.oenb.common.security.web.TomcatSpnegoValve.continueWithChain(TomcatSpnegoValve.java:881)
at at.oenb.common.security.web.TomcatSpnegoValve.invoke(TomcatSpnegoValve.java:508)
at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:128)
at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:102)
at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:567)
at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109)
at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:293)
at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:849)
at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:583)
at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:454)
at java.lang.Thread.run(Thread.java:619)
Created an attachment (id=376)
Example of broken icon