After updating to Tahoe (and this may be just coincidence) all of my cron jobs on my Mac starting erroring out. The only telling error I could find in one of my logs was:

OSError: [Errno 11] Resource deadlock avoided

After double checking almost every permission setting I could find, I discovered that my iCloud Drive settings had switched to “Optimize Storage” I don’t recall making this change so perhaps it was part of the OS upgrade process.

Turning it off in “Settings” seems to have solved all of my cron issues: