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How do you use logrotate with output redirect?

I'm currently running a ruby script which logs its HTTP traffic to stdout. Since I wanted the logs to be persistent, I redirected the output to a log file with ruby ruby_script.rb >> /var/log/ruby_script.log . However, the logs are now getting very large so I wanted to implement logrotate using the following:

"/var/log/ruby_script.log" {
  missingok
  daily
  rotate 10
  dateext
}

However, after running logrotate --force -v ruby_script where "ruby_script" is the name of the logrotate.d configuration file, no new file is created for the script to write to, and it writes to the rotated file instead. I'm guessing this behavior happens because the file descriptor that is passed by >> sticks to the file regardless of moving it, and is unrelated to the filename after the first call. Thus, my question is, what is the correct way to achieve the functionality I'm looking for?

Take a look at option copytruncate .

From man logrotate :

copytruncate : Truncate the original log file to zero size in place after creating a copy, instead of moving the old log file and optionally creating a new one. It can be used when some program cannot be told to close its logfile and thus might continue writing (appending) to the previous log file forever. Note that there is a very small time slice between copying the file and truncating it, so some logging data might be lost. When this option is used, the create option will have no effect, as the old log file stays in place.

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