I doubt it's a Cherokee problem. Do you have a crontab set up on your server?
For example, this is what I have in my unix crontab (not web2py crontab). Cron is still a little confusing to me. MAILTO=c...@myserver.com 0-59/1 * * * * cd /var/web2py && python web2py.py -C -D 1 > /dev/null 2>&1
