Navigate to the Message Icon on the lower navigation pane.
On Inbox, either tap the ">" on a student, or go to the "+" Icon to create a new message.
Next tap the ">" Icon next to the Pupils name that you want to send a message to.
This will now bring up the In-App Messages between you and your Pupil. You can type a message to the Pupil and tap send, this will go to out to them and they will receive a notification, once they tap the notification they will open Total Drive on the Message.