Hi @Kate-And-Rory0
When you create a scheduled message you have to attach it to a listing, or it will not be sent to guests. As long as your scheduled messages are attached to your listing, any future guests should receive the message, even if they booked long in advance of arrival date. Many hosts create schedule messages, but forget to attach them to their listing (I have done this myself...oops).This feature is more applicable if you have multiple listings, but you still have to attach it even if you have only one. Once you attach the scheduled message, you get a callout that says the number of reservations it applies to: