When Work Orders with duration requirements that exceed what any resource has capacity for in one day, the Booking Suggestions control stops suggesting bookings and requires the user to open the scheduling assistant to generate multiple daily bookings to satisfy the requirement.

Opening the schedule Assistant and selecting a resource, the Create Booking pane does not take into account the duration, Resource's work hours or the Window End Date so it defaults the Start and End times to the same day.

Enabling the Quick Book feature to handle Multi-Day bookings would also solve this issue.