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Designing shift plans represents a difficult but interesting task because they must satisfy various, often conflicting, requirements. In this article, we address a complex real-world break-scheduling problem for supervisory personnel and present a scheduling system that can help professional planners create high-quality shift plans. Supervisory personnel spend most of their workday in front of computer monitors, addressing critical and constantly changing situations. For employees working under such conditions to always maintain high levels of concentration, it's essential that they take occasional breaks. Usually, the amount of break time, as well as the position and duration of breaks within their work time (shift) are regulated by labor rules that must be satisfied by a feasible shift plan. Moreover, to guarantee effective supervision, a minimum number of employees must be working at any given time.