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FAIL_MAIL_OVER_500_MILES=TRUE – Unsung
Marcin Wichary · 2026-05-24 · via Unsung

Here’s a 2002 story from a younger internet, by programmer Trey Harris (link to the original and if you don’t like the classic Usenet formatting – my browser’s reader mode can’t even prettify it! – here’s a nicer-looking format):

“We’re having a problem sending email out of the department.”

“What’s the problem?” I asked.

“We can’t send mail more than 500 miles,” the chairman explained.

I choked on my latte. “Come again?”

“We can’t send mail farther than 500 miles from here,” he repeated. “A little bit more, actually. Call it 520 miles. But no farther.”

It would be easy to assume this is a classic case of pebkac, “problem exists between keyboard and chair,” the derisive term used (supposedly!) by support people, describing naïve public who had a tenuous grasp of technological reality. But the story goes to an unexpected place.

This might be the most widely-shared computer bug story of all time I’ve seen – I just saw a comment from 2008 calling it “oldie but a goodie,“ and it even has an FAQ page that’s actually a really great read. There’s quite a bit of chatter inside about something important to me: the balance between the needs of good storytelling and going deep into technical details:

In the story, I make it sound like it took all of ten minutes from being made aware of the 500-mile email limit and determining a 3 ms light-speed issue. In fact, this took several hours, and quite a bit of detective work. The point is, eventually I came up with that figure, ran units, and gagged on my latte.

You can sense author’s frustration with every nerd trying to “gotcha” him instead of just enjoying the story. Even a younger internet wasn’t without faults.