On the night of Friday 13 to Saturday 14 April 1945, after burning all their documents, the Customs Officers stationed in Harlingen left their buildings on the Voorstraat and Zuidoostersingel roads. Other German units followed their example, withdrawing over the Afsluitdijk causeway or by ship to ‘Festung Holland’ (Fortress Holland), a strategic defense concept and fortified area in the Netherlands designed to protect the port of Rotterdam and other vital infrastructure from a potential Allied invasion during World War II. 

On 14 April, acting police commander Lieutenant P.A. Sanders announced: 
‘By order of the local battle commander, it is announced that it is forbidden to be on the streets without absolute necessity. Standing still is strictly prohibited. In case of violation, military patrols will use their weapons.’ 

That same evening, two civilians were killed: 24-year-old Sijbren Kuiper and his wife, Satske Kuiper-van Ingen. Following the escape of their small dog from their house, Mr. Kuiper asked his wife to call it back. As he opened the door of their small house on Steenhouwersstraat road, he began chatting with his neighbour, who was also standing in his doorway. Satske joined them, meanwhile the dog had returned. A German soldier, positioned at the corner of Steenhouwersstraat, fired his weapon when Mr. Kuiper leaned too far outside the door, killing him instantly. His wife, standing behind him, was wounded on her forehead and taken to the hospital by German forces, where she stayed overnight and later died. Meanwhile their baby, Piet, was left alone in his bed. Later that night  their neighbours, the Koster family, took him in. 

On Saturday 14 and Sunday 15 April, a chaotic procession of retreating German soldiers, with fleeing Dutch collaborators, Nationaal-Socialistische Beweging members (Dutch National Socialist Movement), Landwachters (members of the Landwacht, Dutch paramilitary organisation founded by the Nazi occupiers), and other traitors passed through Harlingen toward the Afsluitdijk causeway. They travelled by car, horse and wagon, bicycle, and on foot. Some local farmers were forced to transport them, after those from Dantumadeel municipality were allowed to return home after reaching Harlingen. Residents noted that many of the retreating German soldiers were very young. 

On Sunday 15 April, the population was only permitted on the streets except between 16:00 and 18:00, to buy supplies. That same day, the remaining German troops in Harlingen began acts of destruction, which escalated the next day and the bridges on the Midlumerweg and Kimswerderweg roads were blown up. 

Despite the curfew, on realising that German forces were barely enforcing it, many residents looted abandoned German buildings. This included the cold storage warehouse where pork had been stored and a freight train loaded with 40+ cheeses. Some even stole large coal briquettes from the locomotive tender. These actions were risky, as about 500 German soldiers were still present in Harlingen at the time.