Well. Turns out that cron does in fact catch up on jobs that have a specific hour set if the system time jumps forward by up to three hours. So for some reason, it didn't save the system time when rebooting, came back to a time before the reboot cronjob, then adjusted the system time and until 06:14, cron kept executing the reboot cronjob after the system time had been set. 🤦♂️