The (middle) school building is called Skygningen in Herlovian slang and is one of the school’s oldest buildings. The ground floor contains class rooms for the middle school students, grades 7 through 9, while the first and second floors are organized as student houses/dormitories for students in grades 9, 10 and the high school/IB. The students in Skygningen are divided into Skygningen Øst (East) and Skygningen Vest (West) which both have rooms on the first and second floors. Most students stay in double rooms but all students in 2.g and 3.g have single rooms.
The dorm teacher for Skygningen Øst is Sammy Sieck, who came to Herlufsholm to teach in 2010, but who himself is also a graduate of Herlufsholm. Sammy lives in his apartment with his dogs and twin daughters Hannah and Liva, who both are students at Herlufsholm.