Over the past few weeks while working with client servers running Ubuntu 14.04 LTS, we noticed that the Dynamic MOTD system seems to be outdated when logging in via ssh. While this is a minor annoyance, it needed to be fixed. After a quick Google search, we came across this source which explains how to fix the problem. As pictured below, the solution is to log on to your server as root. Once logged on, navigate to /etc/pam.d/sshd and search for “noupdate” and then remove it and save the file. 
Now close your session and re-open a new one and you will notice that your Dynamic MOTD is now working like it is supposed to. On a side note, if you are running Debian Server and would like a Dynamic MOTD, see our article Debian Wheezy Dynamic MOTD.