We have the same issue. Using "delaycompress" suppresses the "gzip:
stdin: file size changed while zipping" error but upstart will continue
to write on .1 file until this is actually gzipped, which is quite
annoying.

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https://bugs.launchpad.net/bugs/1350782

Title:
  Upstart does not reopen /var/log/upstart/* logfiles upon log rotation

Status in upstart package in Ubuntu:
  Confirmed

Bug description:
  Note: this issue is reported from a 12.04 system, but I've confirmed
  the same behavior on a 14.04 system.

  Logrotate configuration for Upstart logs has no postrotate action:

  /var/log/upstart/*.log {
          daily
          missingok
          rotate 7
          compress
          notifempty
        nocreate
  }

  As a result, when logs are rotated, upstart keeps open handles on
  deleted log files instead of reopening the new log files:

  # lsof -p1 | fgrep /var/log/upstart
  . . .
  init      1 root    8w   REG              253,1       62  789436 
/var/log/upstart/dbus.log.1 (deleted)
  . . .

  From this point on, all subsequent log messages are lost, delivered
  into a deleted file.

  I could not find a way to get the upstart init process to reopen its
  log files, short of restarting _all_ services that log to
  /var/log/upstart/*.log files, which does not seem like a good solution
  at all.

  ProblemType: Bug
  DistroRelease: Ubuntu 12.04
  Package: upstart 1.5-0ubuntu7.2
  ProcVersionSignature: Ubuntu 3.2.0-60.91-generic 3.2.55
  Uname: Linux 3.2.0-60-generic x86_64
  ApportVersion: 2.0.1-0ubuntu17.6
  Architecture: amd64
  Date: Thu Jul 31 10:43:25 2014
  InstallationMedia: Ubuntu-Server 10.04.4 LTS "Lucid Lynx" - Release amd64 
(20120214.2)
  MarkForUpload: True
  ProcEnviron:
   LC_CTYPE=en_US.UTF-8
   TERM=xterm-256color
   PATH=(custom, no user)
   LANG=en_GB.UTF-8
   SHELL=/bin/bash
  SourcePackage: upstart
  UpgradeStatus: Upgraded to precise on 2013-10-23 (280 days ago)

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