Yesterday, this story on Wired was making the rounds: How a Google Headhunter’s E-mail Unraveled a Massive Net Security Hole. Sure, the title is probably hyperbole, but it is an interesting story. At a high level, mathematician Zach Harris noticed that emails from Google – and from several other prominent domains including eBay, PayPal, Yahoo, Amazon, etc. – could be spoofed.

Anyone who has ever run telnet to port 25 and sent an email from or knows that email has always been pretty easy to spoof. Given the rise in unsolicited emails also known as spam, something had to be done. In 2006, a working group was founded to try and create a standard that would make email harder to spoof. It is called  DomainKeys Identified Mail or DKIM. The way DKIM works is that the sending email server applies a digital signature to the mail message headers (completely transparent to the user). The public key which can be used to verify the signature appears in the sending email server’s DNS record.

Since it uses some fancy technology like a digital signature and relies on DNS – a core capability of the internet – email with a valid DKIM signature can generally be trusted that it is legitimately from the domain listed in the From field… Well, that is if you’re doing DKIM correctly.

Mr. Harris found that the DKIM signatures for a number of popular domains used such weak cryptography that it was very easily cracked. While the DKIM standard calls for 1024 bit keys, he found popular domains with 768 bit, 512 bit, and even 384 bit keys. As he points out in the article, he was able to crack the 384 bit keys on his laptop, and for $75 he cracked some 512 bit keys by outsourcing the computing power to Amazon Web Services.

The best quote in the entire article, and the reason I bring this story to your attention is the following:

“People who use cryptographic tools need to realize that local configurations need to be maintained just like software updates need to be maintained,” he says. “In 1998 it was an academic breakthrough of great concerted effort to crack a 512 bit key. Today little old me can do it by myself in 72 hours on AWS. The field of cryptography keeps developing and breaking new ground just like everything else, and you can’t just install a private key, or select a hash algorithm, and expect it to be good forever.”

Wise words, indeed. If connected to any network, you must consider your operating system, your software, and your cryptographic algorithms and keys all as perishable items. They need to be examined for mold and rot periodically, and replaced when necessary. You can no longer afford to “set and forget” anything and consider it dependable.

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