What's the trick to guarantee the booking confirmation message is sent before the check-in message for last-minute bookings?

There's no trick to this as there's no real concept of what message should send first.

What we recommend is to create a last-minute booking message which contains everything you need rather than having 2 separate messages.

For this to work, don't send last-minute bookings the check-in instructions (keep the 'send this message to last-minute bookings' option unchecked and only send the last-minute booking message if the booking lead time is x days before arrival. x days being the same number as what you set your check-in message to send (eg. 1 day before arrival).

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