A google search turned up this as the most likely candidate for my logrotate+gzip issues.
I'm going to try this for a workaround: /var/log/upstart/*.log { daily missingok rotate 7 compress notifempty nocreate # Added by wjd 2017-03 for launchpad bug #1350782 delaycompress sharedscripts postrotate lsof | awk '/ \/var\/log\/upstart\/.*\.log.+/{print $9}' | sed -e 's#.*/##;s#\..*##' | xargs -IX service X restart >/dev/null endscript } -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to upstart in Ubuntu. 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) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/upstart/+bug/1350782/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp