The word "winkle" comes from periwinkle, the name of a marine or freshwater snail. Periwinkle comes from Latin pina a name of a mussel and the Old English wincle, a snail shell.
In World War I, personnel of the Allied Powers found their duty of finding and removing the enemy from the trenches analogous to extracting a well-entrenched snail. They began using winkle to describe their effort.
The action of "winkling the enemy out" extended to other situations, such as "winkling information out of someone."
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