On 9 June "Prins Olav" caught up with the fellow "Hurtigruten" steamer "Ariadne". The two unarmed Norwegian vessels sailed together throughout the day. At 22:30 the ships were discovered by six "Luftwaffe" Heinkel He 111 bombers from the "II. Gruppe" of "Kampfgeschwader 26", despatched from Værnes Air Station near Trondheim to search for ships trying to escape from Northern Norway, and came under attack. After managing to avoid being hit for more than an hour by evasive manoeuvring at full speed, dodging 14 bombs, "Prins Olav" suffered a near miss which damaged her machinery and left her dead in the water. The crew abandoned ship while being strafed by the German aircraft. Shortly after the crew had boarded life boats and left the ship, "Prins Olav" was struck by two bombs in the stern and caught fire before later sinking at . One crew member was killed in the sinking, while four others were wounded. In all, 36 people survived the sinking of "Prins Olav".