Germany's MV Werften shipyard group has filed for bankruptcy after the government and owner Genting Hong Kong failed to agree a rescue deal.
The move means an uncertain future for 2,000 workers and a multi-billion-dollar orderbook of 11 cruise ships contracted by Genting for its Asian operations.
The state of Mecklenburg-Vorpommern's prime minister, Manuela Schwesig, spoke of "bitter news" for the whole country, according to the NDR website.