I'm not using keys. Just using username and password. i think it's related to this line.
Dec 29 00:39:00 webserv2 jk_chrootsh: abort, effective user ID is not 0, possibly jk_chrootsh is not setuid root
Dec 29 00:39:00 webserv2 systemd-logind: Removed session 25.
or maybe the process run level is to low. If it were a key issue it wouldn't work with jailkit disabled.