I think on a restart it flushes/writes the entries to the log file if the option is ticked.
The log files are per month. So if it did reread the log file back in you’d have a months worth of logs.
If you think it’s worthwhile it might’ve worth emailing support with your request. For me I just use a util called cmtrace.exe to open the saved log files, the util gives a nicer view than notepad.