Facebook’s Ad-Targeting Problem, Captured in a Literal Shade of Gray

For a sense of the dilemma confronting Facebook over its ad-targeting system, consider the following word: confederate. As of Sept 27, any prospective advertiser who typed that word into Facebook’s ad-targeting engine would be prompted to distribute their ad to a potential audience of more than four million users who had indicated an interest in the Confederate States of America.

The social network recently grappled with revelations that advertisers were able to target Facebook users who used terms like “Jew hater” to describe themselves. But even after the company took steps to shut down those clearly offensive categories, other targeting terms remain that fall into a gray area. That includes categories like Confederate States, which are legitimate in principle but can be potentially problematic or misused in practice. It illustrates the blurry lines and policing challenge that confront Facebook in its ad targeting. And after a year in which the social network has accepted more responsibility to crack down on false or offensive material, and last week, when the company twice announced new measures to prevent abuses by advertisers, some experts said the scale of that challenge is only starting to become apparent.