Two infosec blunders that betrayed the Russian spy ring

From what little we do know though - ie the content of the FBI's criminal complaints - it's apparent the group's technology tradecraft was not as sharp as you might expect from deep cover spies.  http://documents.nytimes.com/criminal-complaints-from-the-justice-department#document/

Here we present their two most glaring infosec failings.

* Return of the MAC

Anna Chapman and her UN-based Russian government handler allegedly held ten meetings around Manhattan between January and June. They would not make overt contact but would exchange data over an ad hoc Wi-Fi network.

Chapman and the offical made things easy for their watchers, however, by using the same laptops with the same MAC addresses every time. It meant the FBI could tell whenever the pair were in contact simply by following them and using an off-the shelf Wi-Fi network analyser package to match the two MAC addresses.

The pair could have simply used multiple machines, or used any one of an array of utilities that would have allowed them to spoof their MAC addresses. Instead, the FBI's complaint that Chapman was an undeclared agent of a foreign government draws heavily on correlating the two numbers broadcast between her laptop and her handler's.

Chapman knew enough about countering surveillance to buy a "burner" mobile phone and international calling card under a fake name to contact Moscow, apparently after she suspected her new handler (in fact an undercover FBI agent) was not all he seemed last weekend. But that was after she had given him her laptop for repairs.

There are plenty of other options of course for more secure coffee shop wireless data exchanges; post your idea in comments.

* Password pants down

In 2005, the FBI obtained a warrant for a covert search of Richard and Cynthia Murphy's home in Montclair, New Jersey.

Agents made forensic copies of "a set of computer disks" and took photographs of documents. The disks are described in court documents as "password protected" - it's unclear whether the password was required to decrypt the disks, or simply to use the steganography program they contained.

That open question is academic, however, because the couple had helpfully written down the 27-character password for the FBI's photographers. "The paper said "alt", "control", and "e", and set forth a string of 27 characters," the court documents explain. "Using these 27 characters as a password, technicians have been able successfully to access a software program."

This was apparently a crucial development in the investigation, because access to the steganography programme, which had allegedly been developed by Russia's foreign intelligence service and is not available commercially, enabled the FBI to easily find and decrypt more than one hundred hidden messages on the Murphy's hard-drive, which was also forensically copied during the raid.

Of course, it's possible investigators would have unlocked the programme anyway using brute force or other attacks, but by writing their passwords down on paper and keeping it at home the "Murphys" made it comically easy for them. The resulting cache of secret messages apparently forms the basis of much of US knowledge about the Russian spy ring.

Such blundering will do little to quell those speculating the spy ring was some sort of dastardly setup by Moscow Centre to occupy US counter-espionage investigators. Real cynics will suggest the episode proves spies are just like any other users. ®