Also, pulled from the cherokee website, you'll want to use ssl (most likely) and they instruct you to also install another package for that. sudo apt-get install libcherokee-mod-libssl You'll also have to point to the ssl key and certificate, but that was the piece I was missing, even though I had openssl done, and created the key and cert. For reference, copy and paste this to setup they key and cert also: openssl req -days 1000 -new -x509 -nodes -out /etc/cherokee/ssl/cherokee.pem -keyout /etc/cherokee/ssl/cherokee.pem