The Expert's View with Jeremy Kirk

Endpoint Security , Information Sharing , Next-Generation Technologies & Secure Development

Lavabit Reboots After FBI Snowden Investigation Fallout

In Theory, Lavabit Email Will Be Tough to Trace or Subpoena
Lavabit Reboots After FBI Snowden Investigation Fallout
The retooled Lavabit is based on the Dark Internet Mail Environment (logo pictured).

Nearly four years after a messy legal tangle with U.S. government, encrypted email provider Lavabit is back.

See Also: ISO/IEC 27001: The Cybersecurity Swiss Army Knife for Info Guardians

Lavabit founder Ladar Levison shut down the relatively obscure, Texas-based company in 2013 after the U.S. government sought its encryption keys through secret court proceedings.

At the time, the U.S. government was hot on the trail of former National Security Agency contractor Edward Snowden, who used Lavabit's email service after he leaked top-secret signals intelligence documents. Rather than provide the U.S. government with the single key that would have unlocked emails sent by Snowden - and potentially every other user - Levison shuttered Lavabit, citing a legal environment that was hostile to users' privacy.

Levison says he is relaunching Lavabit with a revamped architecture, including improvements that should make it harder for anyone but the designated user to access either an email's content or associated metadata.

"With your continued patronage, we will restore privacy and make end-to-end encryption an automatic, ubiquitous and open-source reality," Levison writes on Lavabit's front page.

Resistance in 4-Point Type

Under a secret subpoena and search-and-seizure warrant, Levison was ordered in June 2013 to turn over encryption and SSL keys for government investigators trying to access Snowden's Lavabit account.

Levison opposed turning over Lavabit's master SSL/TLS key. Divulging that key would put at risk the communications of Lavabit's 400,000 users, as it would be possible for the government to decrypt their username and password logins, he maintained.

Failing in his bid to protect those users, Levison reluctantly turned over the key to the government in the form of an 11-page, largely illegible printout with the key's 2,560 characters in four-point type. Needless to say, the FBI was not pleased, and a judge eventually forced Levison to furnish the keys electronically.

In early August 2013, Levison closed Lavabit. He said he wished Lavabit could participate in a discussion on government surveillance powers, but that he was barred from discussing his company's case.

Email: A Leaky Tool

Taking a step back, it's important to remember that email wasn't designed with security in mind. Emailed content is not encrypted by default, and related metadata - such as the subject line and associated email addresses - are not protected.

Innovations such as PGP, short for Pretty Good Privacy, eventually brought encryption to email. Other services called "remailers" popped up to protect metadata, anonymously relaying email and stripping out identifying crumbs. But for less technical users, mastering such services can be a challenge. The end result is that usability trumps security, and the vast majority of today's emails still get sent in unprotected form.

Feeling Trustful, Cautious or Paranoid?

Now, Levison has unveiled two kinds of software that are designed to improve content and metadata security, according to a technical write-up. One is DIME, or the Dark Internet Mail Environment, which is an encryption protocol designed to provide end-to-end encryption. DIME encrypts metadata. The other software is Magma, which is a mail server that implements DIME. Beta versions of both pieces of software are on GitHub.

Of critical importance with encrypted email is how the private key - aka the secret key that can decrypt an email's content - gets stored. DIME has three modes: trustful, cautious and paranoid. The most restricted level, paranoid, means that users manage their own keys, leaving up to them to keep it secure.

The Dark Internet Mail Environment offers three user-selectable modes.

Old Lavabit vs. New Lavabit

Provided that email gets securely encrypted, the issue of whether the SSL/TLS key ultimately gets divulged or stolen doesn't matter as much, Levison writes.

Still, Lavabit has taken steps to make its SSL key more difficult for the government to obtain. Levison writes that the SSL key will be kept in a hardware secure module, which is an ultra-secure device that in theory would be difficult to hack.

Lavabit won't be able to access the key directly. In order to prevent whoever administers the HSM device from accessing the key, Lavabit is setting the password blindly "thus locking us out," he writes.

Still, anyone not comfortable with Lavabit's configuration should use the cautious or paranoid modes, he writes. In paranoid mode, for example, users must manage their keys entirely on their own.

Commercial Appeal?

Lavabit's more locked-down modes are designed to appeal to users who have the most extreme security requirements or worries. But Levison's system also envisions that companies will opt for trustful mode. That mode leaves key management up to Lavabit, with the trade-off being that it's a lot easier for companies to get up and running.

"We envision trustful mode as the mode of choice for businesses, which have regulatory requirements, data retention practices and unique needs like escrow keys. Lavabit's free and open source server, Magma, supports these users," Levison writes.

Email Hacking Dominates the News

The timing of Levison's Lavabit relaunch couldn't be better. The U.S. intelligence community's conclusion that Russian-backed hackers ransacked and released Democratic Party emails should be warning enough that unencrypted email poses a risk to every type of organization (see Did Weak InfoSec Sway Election?).

Historically, however, so many individuals and organizations only reach for strong security improvements after they get burned. Time will tell if many more enterprises will now heed the warnings associated with the hacks of the DNC - and so many others - and embrace encrypted email services, such as Lavabit.

About the Author

Jeremy Kirk

Jeremy Kirk

Executive Editor, Security and Technology, ISMG

Kirk was executive editor for security and technology for Information Security Media Group. Reporting from Sydney, Australia, he created "The Ransomware Files" podcast, which tells the harrowing stories of IT pros who have fought back against ransomware.

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