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Hello, @insanityfarm
I believe this question was already asked in our community and you can check the other question using this link - https://www.digitalocean.com/community/questions/message-of-the-day-motd-not-displayed
"
Is the MOTD displayed when you log in through the remote console? Make sure that your sshd config allows the MOTD to be shown on login:
UsePAM yes
PrintMotd no
Don’t forget to restart the ssh server/daemon after modifying the config file:
sudo service ssh restart
"
Regards, Alex