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Why “Sorry, I don’t know” is sometimes the best answer: The Washington Post’s technology chief on its first AI chatbot
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May 16, 2013, 2:44 p.m.

On Wednesday, the New Yorker launched a Tor- and open-source-based file-sharing tool/tip line called Strongbox meant to allow sources to communicate information to the magazine without fear of it being traced back to them.

Since then, Source has compiled a wealth of context and information, including a litany of responses from across Twitter. Today, Source contacted some experts for further exposition. Writes Jonathan Stray:

I am also concerned that the system may still be too hard to use. The Strongbox web service has a simple, clean interface — and bravo for that — but first the user has to get Tor running. In my experience, even savvy technologists vastly overestimate the number of people who can reliably complete tasks like “download and install this software.” If these users don’t also understand why such drastic measures are necessary, they will find ways to accomplish their goals with much simpler tools — like email. Strongbox cannot help users who are too frustrated to get it working properly.

And then, there is “the big question hanging over any secure dropbox,” writes The New York Times’ Jacob Harris: “Will you get any useful tips?”

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