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Beginning in May 1887, Sally Katzenstein studied at the Düsseldorf Academy of Art, specializing in painting. Until April 1888, he was part of the elementary class of Heinrich Lauenstein. In the student lists, brief comments about him were made: Talent: fair. Diligence and conduct: very good." One year later his artistic skills were rated as "good." In 1888 Sally came for the first time to the island of Sylt for the purpose of studying there with Eugen Dücker's painting class. Landscape studies were supposed to be made on location. The sojourn in Sylt was followed immediately by an eleven-month stay in Florence, so that Sally next returned to Sylt only in 1889 – in order to make his home there. In 1890, in the Ribera artists' salon in Berlin, he exhibited themes related to Sylt for the first time, in regard to which the Vossische Zeitung [a newspaper] praised the simple and austere quality of nature on the island.

The painting was bought - and supposedly even commissioned - for the Imperial Mail Museum by Heinrich von Stephan, the organizer of the German postal system. It shows the evening run of the ice-breaker boat, by means of which the connection to the mainland was maintained in severe winters, when the usual routes through the water or through tidal flatsare blocked by ice floes. This was the only way that mail and medicines, small packages and newspapers could reach the island every now and then. The ice-breaker boat was an open, sturdy vehicle, equipped with runners, which could be pushed over the ice or pulled with straps by four men. It could also be rowed or sailed in those places where the tidal currents had prevented ice formation. The ice-breaker boat was used most frequently in the winter of 1888/89, when the tidal flats had frozen already in November and thawed again only in March. The painting possibly depicts that icy winter, during which 57 of these dangerous trips were undertaken.