As I recall the very first ship sunk by a U-boat in WW2 was a passenger liner (possibly a neutral one). back in the day the rules of engagement were really a farce. After WW1 the rules regarding U-boats were set so that they essentially had to surrender their most powerful weapon: stealth. A U-boat which wanted to sink an enemy merchant ship had to first pull along side it and then board her and ask the captain for papers. Once they had seen the crew safely into their life boats the U-boat could then sink the ship. Now obviously this is entirely unworkable. It was intended to be so.
Whats interesting is that the British started to make following the rules hard before the U-boats even began disregarding them. So called Q-ships were constructed which were just passenger liners and merchant ships which were equipped with sliding bulkheads that hid weapons designed to destroy U-boats as they came along side to board her. Who broke the rules first? As the victors the Brits say Germany but I'd beg to differ.
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