Doing some research I found this thread. Basically the solution there was to add a new user, and set up the crontab with that user.
A few months back I did some config with the crontab for the root user that got wiped after an automatic firmware update, but not sure if this approach will fix it since I haven’t done much with it since.
I think what happens is the system resets the root user settings back to the defaults after a firmware update, but maybe on any reboot. If that holds true then making a separate cronjob user would make sense as a solution