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E-Mail Vulnerabilities and Disclosure

Last week, researchers disclosed vulnerabilities in a large number of encrypted e-mail clients: specifically, those that use OpenPGP and S/MIME, including Thunderbird and AppleMail. These are serious vulnerabilities: An attacker who can alter mail sent to a vulnerable client can trick that client into sending a copy of the plaintext to a web server controlled by that attacker. The story of these vulnerabilities and the tale of how they were disclosed illustrate some important lessons about security vulnerabilities in general and e-mail security in particular.

But first, if you use PGP or S/MIME to encrypt e-mail, you need to check the list on this page and see if you are vulnerable. If you are, check with the vendor to see if they’ve fixed the vulnerability. (Note that some early patches turned out not to fix the vulnerability.) If not, stop using the encrypted e-mail program entirely until it’s fixed. Or, if you know how to do it, turn off your e-mail client’s ability to process HTML e-mail or — even better — stop decrypting e-mails from within the client. There’s even more complex advice for more sophisticated users, but if you’re one of those, you don’t need me to explain this to you.

Consider your encrypted e-mail insecure until this is fixed.

All software contains security vulnerabilities, and one of the primary ways we all improve our security is by researchers discovering those vulnerabilities and vendors patching them. It’s a weird system: Corporate researchers are motivated by publicity, academic researchers by publication credentials, and just about everyone by individual fame and the small bug-bounties paid by some vendors.

Software vendors, on the other hand, are motivated to fix vulnerabilities by the threat of public disclosure. Without the threat of eventual publication, vendors are likely to ignore researchers and delay patching. This happened a lot in the 1990s, and even today, vendors often use legal tactics to try to block publication. It makes sense; they look bad when their products are pronounced insecure.

Over the past few years, researchers have started to choreograph vulnerability announcements to make a big press splash. Clever names — the e-mail vulnerability is called “Efail” — websites, and cute logos are now common. Key reporters are given advance information about the vulnerabilities. Sometimes advance teasers are released. Vendors are now part of this process, trying to announce their patches at the same time the vulnerabilities are announced.

This simultaneous announcement is best for security. While it’s always possible that some organization — either government or criminal — has independently discovered and is using the vulnerability before the researchers go public, use of the vulnerability is essentially guaranteed after the announcement. The time period between announcement and patching is the most dangerous, and everyone except would-be attackers wants to minimize it.

Things get much more complicated when multiple vendors are involved. In this case, Efail isn’t a vulnerability in a particular product; it’s a vulnerability in a standard that is used in dozens of different products. As such, the researchers had to ensure both that everyone knew about the vulnerability in time to fix it and that no one leaked the vulnerability to the public during that time. As you can imagine, that’s close to impossible.

Efail was discovered sometime last year, and the researchers alerted dozens of different companies between last October and March. Some companies took the news more seriously than others. Most patched. Amazingly, news about the vulnerability didn’t leak until the day before the scheduled announcement date. Two days before the scheduled release, the researchers unveiled a teaser — honestly, a really bad idea — which resulted in details leaking.

After the leak, the Electronic Frontier Foundation posted a notice about the vulnerability without details. The organization has been criticized for its announcement, but I am hard-pressed to find fault with its advice. (Note: I am a board member at EFF.) Then, the researchers published — and lots of press followed.

All of this speaks to the difficulty of coordinating vulnerability disclosure when it involves a large number of companies or — even more problematic — communities without clear ownership. And that’s what we have with OpenPGP. It’s even worse when the bug involves the interaction between different parts of a system. In this case, there’s nothing wrong with PGP or S/MIME in and of themselves. Rather, the vulnerability occurs because of the way many e-mail programs handle encrypted e-mail. GnuPG, an implementation of OpenPGP, decided that the bug wasn’t its fault and did nothing about it. This is arguably true, but irrelevant. They should fix it.

Expect more of these kinds of problems in the future. The Internet is shifting from a set of systems we deliberately use — our phones and computers — to a fully immersive Internet-of-things world that we live in 24/7. And like this e-mail vulnerability, vulnerabilities will emerge through the interactions of different systems. Sometimes it will be obvious who should fix the problem. Sometimes it won’t be. Sometimes it’ll be two secure systems that, when interact in a particular way, cause an insecurity. In April, I wrote about a vulnerability that arose because Google and Netflix make different assumptions about e-mail addresses. I don’t even know who to blame for that one.

It gets even worse. Our system of disclosure and patching assumes that vendors have the expertise and ability to patch their systems, but that simply isn’t true for many of the embedded and low-cost Internet of things software packages. They’re designed at a much lower cost, often by offshore teams that come together, create the software, and then disband; as a result, there simply isn’t anyone left around to receive vulnerability alerts from researchers and write patches. Even worse, many of these devices aren’t patchable at all. Right now, if you own a digital video recorder that’s vulnerable to being recruited for a botnet — remember Mirai from 2016? — the only way to patch it is to throw it away and buy a new one.

Patching is starting to fail, which means that we’re losing the best mechanism we have for improving software security at exactly the same time that software is gaining autonomy and physical agency. Many researchers and organizations, including myself, have proposed government regulations enforcing minimal security-standards for Internet-of-things devices, including standards around vulnerability disclosure and patching. This would be expensive, but it’s hard to see any other viable alternative.

Getting back to e-mail, the truth is that it’s incredibly difficult to secure well. Not because the cryptography is hard, but because we expect e-mail to do so many things. We use it for correspondence, for conversations, for scheduling, and for record-keeping. I regularly search my 20-year e-mail archive. The PGP and S/MIME security protocols are outdated, needlessly complicated and have been difficult to properly use the whole time. If we could start again, we would design something better and more user friendly¬≠but the huge number of legacy applications that use the existing standards mean that we can’t. I tell people that if they want to communicate securely with someone, to use one of the secure messaging systems: Signal, Off-the-Record, or — if having one of those two on your system is itself suspicious — WhatsApp. Of course they’re not perfect, as last week’s announcement of a vulnerability (patched within hours) in Signal illustrates. And they’re not as flexible as e-mail, but that makes them easier to secure.

This essay previously appeared on

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Details on a New PGP Vulnerability

A new PGP vulnerability was announced today. Basically, the vulnerability makes use of the fact that modern e-mail programs allow for embedded HTML objects. Essentially, if an attacker can intercept and modify a message in transit, he can insert code that sends the plaintext in a URL to a remote website. Very clever.

The EFAIL attacks exploit vulnerabilities in the OpenPGP and S/MIME standards to reveal the plaintext of encrypted emails. In a nutshell, EFAIL abuses active content of HTML emails, for example externally loaded images or styles, to exfiltrate plaintext through requested URLs. To create these exfiltration channels, the attacker first needs access to the encrypted emails, for example, by eavesdropping on network traffic, compromising email accounts, email servers, backup systems or client computers. The emails could even have been collected years ago.

The attacker changes an encrypted email in a particular way and sends this changed encrypted email to the victim. The victim’s email client decrypts the email and loads any external content, thus exfiltrating the plaintext to the attacker.

A few initial comments:

1. Being able to intercept and modify e-mails in transit is the sort of thing the NSA can do, but is hard for the average hacker. That being said, there are circumstances where someone can modify e-mails. I don’t mean to minimize the seriousness of this attack, but that is a consideration.

2. The vulnerability isn’t with PGP or S/MIME itself, but in the way they interact with modern e-mail programs. You can see this in the two suggested short-term mitigations: “No decryption in the e-mail client,” and “disable HTML rendering.”

3. I’ve been getting some weird press calls from reporters wanting to know if this demonstrates that e-mail encryption is impossible. No, this just demonstrates that programmers are human and vulnerabilities are inevitable. PGP almost certainly has fewer bugs than your average piece of software, but it’s not bug free.

3. Why is anyone using encrypted e-mail anymore, anyway? Reliably and easily encrypting e-mail is an insurmountably hard problem for reasons having nothing to do with today’s announcement. If you need to communicate securely, use Signal. If having Signal on your phone will arouse suspicion, use WhatsApp.

I’ll post other commentaries and analyses as I find them.

EDITED TO ADD (5/14): News articles.

Slashdot thread.

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Critical PGP Vulnerability

EFF is reporting that a critical vulnerability has been discovered in PGP and S/MIME. No details have been published yet, but one of the researchers wrote:

We’ll publish critical vulnerabilities in PGP/GPG and S/MIME email encryption on 2018-05-15 07:00 UTC. They might reveal the plaintext of encrypted emails, including encrypted emails sent in the past. There are currently no reliable fixes for the vulnerability. If you use PGP/GPG or S/MIME for very sensitive communication, you should disable it in your email client for now.

This sounds like a protocol vulnerability, but we’ll learn more tomorrow.

News articles.

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Virginia Beach Police Want Encrypted Radios

This article says that the Virginia Beach police are looking to buy encrypted radios.

Virginia Beach police believe encryption will prevent criminals from listening to police communications. They said officer safety would increase and citizens would be better protected.

Someone should ask them if they want those radios to have a backdoor.

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Ray Ozzie’s Encryption Backdoor

Last month, Wired published a long article about Ray Ozzie and his supposed new scheme for adding a backdoor in encrypted devices. It’s a weird article. It paints Ozzie’s proposal as something that “attains the impossible” and “satisfies both law enforcement and privacy purists,” when (1) it’s barely a proposal, and (2) it’s essentially the same key escrow scheme we’ve been hearing about for decades.

Basically, each device has a unique public/private key pair and a secure processor. The public key goes into the processor and the device, and is used to encrypt whatever user key encrypts the data. The private key is stored in a secure database, available to law enforcement on demand. The only other trick is that for law enforcement to use that key, they have to put the device in some sort of irreversible recovery mode, which means it can never be used again. That’s basically it.

I have no idea why anyone is talking as if this were anything new. Several cryptographers have already explained explained why this key escrow scheme is no better than any other key escrow scheme. The short answer is (1) we won’t be able to secure that database of backdoor keys, (2) we don’t know how to build the secure coprocessor the scheme requires, and (3) it solves none of the policy problems around the whole system. This is the typical mistake non-cryptographers make when they approach this problem: they think that the hard part is the cryptography to create the backdoor. That’s actually the easy part. The hard part is ensuring that it’s only used by the good guys, and there’s nothing in Ozzie’s proposal that addresses any of that.

I worry that this kind of thing is damaging in the long run. There should be some rule that any backdoor or key escrow proposal be a fully specified proposal, not just some cryptography and hand-waving notions about how it will be used in practice. And before it is analyzed and debated, it should have to satisfy some sort of basic security analysis. Otherwise, we’ll be swatting pseudo-proposals like this one, while those on the other side of this debate become increasingly convinced that it’s possible to design one of these things securely.

Already people are using the National Academies report on backdoors for law enforcement as evidence that engineers are developing workable and secure backdoors. Writing in Lawfare, Alan Z. Rozenshtein claims that the report — and a related New York Times story — “undermine the argument that secure third-party access systems are so implausible that it’s not even worth trying to develop them.” Susan Landau effectively corrects this misconception, but the damage is done.

Here’s the thing: it’s not hard to design and build a backdoor. What’s hard is building the systems — both technical and procedural — around them. Here’s Rob Graham:

He’s only solving the part we already know how to solve. He’s deliberately ignoring the stuff we don’t know how to solve. We know how to make backdoors, we just don’t know how to secure them.

A bunch of us cryptographers have already explained why we don’t think this sort of thing will work in the foreseeable future. We write:

Exceptional access would force Internet system developers to reverse “forward secrecy” design practices that seek to minimize the impact on user privacy when systems are breached. The complexity of today’s Internet environment, with millions of apps and globally connected services, means that new law enforcement requirements are likely to introduce unanticipated, hard to detect security flaws. Beyond these and other technical vulnerabilities, the prospect of globally deployed exceptional access systems raises difficult problems about how such an environment would be governed and how to ensure that such systems would respect human rights and the rule of law.

Finally, Matthew Green:

The reason so few of us are willing to bet on massive-scale key escrow systems is that we’ve thought about it and we don’t think it will work. We’ve looked at the threat model, the usage model, and the quality of hardware and software that exists today. Our informed opinion is that there’s no detection system for key theft, there’s no renewability system, HSMs are terrifically vulnerable (and the companies largely staffed with ex-intelligence employees), and insiders can be suborned. We’re not going to put the data of a few billion people on the line an environment where we believe with high probability that the system will fail.

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LC4: Another Pen-and-Paper Cipher

Interesting symmetric cipher: LC4:

Abstract: ElsieFour (LC4) is a low-tech cipher that can be computed by hand; but unlike many historical ciphers, LC4 is designed to be hard to break. LC4 is intended for encrypted communication between humans only, and therefore it encrypts and decrypts plaintexts and ciphertexts consisting only of the English letters A through Z plus a few other characters. LC4 uses a nonce in addition to the secret key, and requires that different messages use unique nonces. LC4 performs authenticated encryption, and optional header data can be included in the authentication. This paper defines the LC4 encryption and decryption algorithms, analyzes LC4’s security, and describes a simple appliance for computing LC4 by hand.

Almost two decades ago I designed Solitaire, a pen-and-paper cipher that uses a deck of playing cards to store the cipher’s state. This algorithm uses specialized tiles. This gives the cipher designer more options, but it can be incriminating in a way that regular playing cards are not.

Still, I like seeing more designs like this.

Hacker News thread.

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IoT Inspector Tool from Princeton

Researchers at Princeton University have released IoT Inspector, a tool that analyzes the security and privacy of IoT devices by examining the data they send across the Internet. They’ve already used the tool to study a bunch of different IoT devices. From their blog post:

Finding #3: Many IoT Devices Contact a Large and Diverse Set of Third Parties

In many cases, consumers expect that their devices contact manufacturers’ servers, but communication with other third-party destinations may not be a behavior that consumers expect.

We have found that many IoT devices communicate with third-party services, of which consumers are typically unaware. We have found many instances of third-party communications in our analyses of IoT device network traffic. Some examples include:

  • Samsung Smart TV. During the first minute after power-on, the TV talks to Google Play, Double Click, Netflix, FandangoNOW, Spotify, CBS, MSNBC, NFL, Deezer, and Facebook¬≠even though we did not sign in or create accounts with any of them.

  • Amcrest WiFi Security Camera. The camera actively communicates with using HTTPS. QuickDDNS is a Dynamic DNS service provider operated by Dahua. Dahua is also a security camera manufacturer, although Amcrest’s website makes no references to Dahua. Amcrest customer service informed us that Dahua was the original equipment manufacturer.

  • Halo Smoke Detector. The smart smoke detector communicates with Xively offers an MQTT service, which allows manufacturers to communicate with their devices.

  • Geeni Light Bulb. The Geeni smart bulb communicates with, which is operated by TuYa, a China-based company that also offers an MQTT service.

We also looked at a number of other devices, such as Samsung Smart Camera and TP-Link Smart Plug, and found communications with third parties ranging from NTP pools (time servers) to video storage services.

Their first two findings are that “Many IoT devices lack basic encryption and authentication” and that “User behavior can be inferred from encrypted IoT device traffic.” No surprises there.

Boingboing post.

Related: IoT Hall of Shame.

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Two NSA Algorithms Rejected by the ISO

The ISO has rejected two symmetric encryption algorithms: SIMON and SPECK. These algorithms were both designed by the NSA and made public in 2013. They are optimized for small and low-cost processors like IoT devices.

The risk of using NSA-designed ciphers, of course, is that they include NSA-designed backdoors. Personally, I doubt that they’re backdoored. And I always like seeing NSA-designed cryptography (particularly its key schedules). It’s like examining alien technology.

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