diff --git a/config/clock.rb b/config/clock.rb
index 7183123f53a..2674495f056 100644
--- a/config/clock.rb
+++ b/config/clock.rb
@@ -7,6 +7,7 @@ require_relative 'environment'
 
 def setup_log
   Clockwork.configure do |config|
+    config[:logger].close
     config[:logger] = Logger.new(ENV["CLOCK_LOG"])
   end if ENV["CLOCK_LOG"]
 end
diff --git a/config/logrotate.conf b/config/logrotate.conf
index 1b29b530e7c..25d50d0081c 100644
--- a/config/logrotate.conf
+++ b/config/logrotate.conf
@@ -13,13 +13,15 @@ create 0644
 /home/discourse/discourse/log/clockwork.log
 {
     postrotate
-        pkill -f clockwork -HUP
+        pkill -HUP -f clockwork
     endscript
 }
 /home/discourse/discourse/log/sidekiq.log
 {
+    # Should we just kill sidekiq?
+    # https://github.com/mperham/sidekiq/issues/1008
     postrotate
-        pkill -f sidekiq -USR2
+        pkill -USR2 -f sidekiq
     endscript
 }
 /home/discourse/discourse/log/production.log
@@ -33,6 +35,6 @@ create 0644
 /home/discourse/discourse/log/thin*.log
 {
     postrotate
-        pkill -f 'thin server' -USR1
+        pkill -USR1 -f 'thin server'
     endscript
 }