No time data is displayed in the 'Created' column in the Windows native client session list. Observed in 4.14 and forward.
This bug doesn't appear on Linux nor macOS, as time data is properly displayed there.
To enable the multi session list, you need to allow multiple sessions per user:
sudo tl-config /vsmserver/max_sessions_per_user=0
sudo systemctl restart vsmserver
Configure the “Reconnect policy” in the client with “Always ask how multiple sessions should be handled”.
Then, when you are about to start your second session for the same user, you will be presented with the session list.