SOLVED: Leaving this up but was just solved by restarting the service rather than rebuilding it.
So far I’m seeing nothing in the logs that indicate any sort of error across either of my projects. I’ve double checked my deployment hours and I’m still perfectly fine on that end. My cron-job still goes through and correctly pings the site as well. Currently looking into the Cloudflare troubleshooting but just wanted to put this up in case there were any other eyes that have experienced this before.