It's a core issue from what I see. Fixed the component and added my Example

I see the same issue with pluginSetupWizard.js

Jul 07, 2016 11:43:38 AM org.eclipse.jetty.util.log.JavaUtilLog warn
WARNING: /jenkins/static/ba556f68/jsbundles/pluginSetupWizard.js
java.io.IOException: failed to deflate: error=-5 avail_out=265
	at com.jcraft.jzlib.DeflaterOutputStream.deflate(DeflaterOutputStream.java:140)
	at com.jcraft.jzlib.DeflaterOutputStream.finish(DeflaterOutputStream.java:111)
	at com.jcraft.jzlib.DeflaterOutputStream.close(DeflaterOutputStream.java:117)
	at org.kohsuke.stapler.compression.FilterServletOutputStream.close(FilterServletOutputStream.java:36)
	at org.kohsuke.stapler.compression.CompressionServletResponse.close(CompressionServletResponse.java:67)
	at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:63)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
	at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
	at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
	at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:585)
	at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
	at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:553)
	at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:223)
	at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1127)

Problem persists after a restart? Kinda sounds like an issue in the static cache, with it caching corrupt copies of the resources.

teilo pointed to https://github.com/ymnk/jzlib/blob/master/src/main/java/com/jcraft/jzlib/Deflater.java#L57 . So it's likely a buffer error

Hi,
I got a similar error after the last upgrade of Jenkins to 2.7.1

WARNING: /adjuncts/944d0d57/org/kohsuke/stapler/jquery/jquery.full.js
java.io.IOException: failed to deflate: error=-5 avail_out=260
at com.jcraft.jzlib.DeflaterOutputStream.deflate(DeflaterOutputStream.java:140)
at com.jcraft.jzlib.DeflaterOutputStream.finish(DeflaterOutputStream.java:111)
at com.jcraft.jzlib.DeflaterOutputStream.close(DeflaterOutputStream.java:117)
at org.kohsuke.stapler.compression.FilterServletOutputStream.close(FilterServletOutputStream.java:36)
at org.kohsuke.stapler.compression.CompressionServletResponse.close(CompressionServletResponse.java:67)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:63)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:585)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:553)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:223)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1127)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:515)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:185)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1061)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:97)
at org.eclipse.jetty.server.Server.handle(Server.java:499)
at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:311)
at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:257)
at org.eclipse.jetty.io.AbstractConnection$2.run(AbstractConnection.java:544)
at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)
at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
at java.lang.Thread.run(Unknown Source)