As of this time, it is possible to attach an image to a scheduled message, but no other types of automatic messages, and for rules sending messages until the day of the check-out. Other file types are not supported. Only one image at a time can be attached.

An alternative solution to sending multiple images or other file types to your guests would be:

  1. Upload the file(s) to a cloud storage such as Dropbox or Google Drive.
  2. Set the file sharing permissions to Anyone with the link.
  3. Copy the file URL.
  4. (Optional) Trim or customize the URL using a URL shortener such as bit.ly.
  5. Paste the final URL into your automatic message template.

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