I have an Ubuntu server running at sandbox.plushu.org - if you add your key at http://enter.sandbox.plushu.org, you can connect to the server as firstname.lastname@example.org. You can reset the server by pressing the reset button on http://reset-sandbox.plushu.org.
I have a custom time-sensitive MOTD on this server. The problem that I'm seeing is that this MOTD, when regenerated (via /etc/update-motd/*) at login, is not displayed until the next login. The first time you log in, you will see the MOTD as generated at boot: the next time you log in, you will see the MOTD as generated the last time you logged in.
What is causing this behavior? How can it be fixed so that, on logging in, the MOTD is generated, then displayed?