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I suppose it's hard to say if automated similarity metrics are at fault here, but certainly things did not go as planned :)

Here we have a web page that talks about Hitler and the Nazis. And Google AdWords, to its credit, seems to be pretty good at picking out fun Hitler-related ads to go in the sidebar... but oops, note the ad I've conveniently highlighted in red.

Looks like it's back to sensitivity training for AdWords!

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