Image from EFF

Is e-mail OK for secret stuff?

Image by EFF

Image by EFF

Short answer: No. Slightly longer answer: Maybe, but not without additional protection.

E-mail is one of the oldest and most widely used services on Internet. It was developed during an era when we were comfortably unaware of viruses, worms, spam, e-crime and the NSA. And that is clearly visible in the architecture and blatant lack of security features. Without going deep into technical details, one can conclude that the security of plain e-mail is next to non-existing. The mail standards do by themselves not provide any kind of encryption or verification of the communicating parties’ identity. All this can be done with additional protection arrangements. But are you doing it and do you know how to?

Here’s some points to keep in mind.

  • Hackers or intelligence agencies may tap into the traffic between you and the mail server. This is very serious as it could reveal even your user ID and password, enabling others to log in to the server and read your stored mails. The threat can be mitigated by ensuring that the network traffic is encrypted. Most mail client programs offer an option to use SSL- or TLS-encryption for sent and received mail. See the documentation for your mail program or service provider. If you use webmail in your browser, you should make sure the connection is encrypted. See this article for more details. If it turns out that you can’t use encryption with your current service provider, then start looking for another one promptly.
  • Your mails are stored at the mail server. There are three main points that affect how secure they are there. Your own password and how secret you keep it, the service provider’s security policies and the legislation in the country where the service provider operates. Most ordinary service providers offer decent protection against hackers and other low-resource parties, but less protection against authorities in their home country.
  • Learn how to recognize phishing attacks as that is one of the most common reasons for mail accounts to be compromised.
  • There are some mail service providers that focus purely on secrecy and use some kind of encryption to keep messages secret. Hushmail (Canada) and Mega’s (New Zealand) planned service are good examples. Lavabit and Silent Mail used to provide this kind of service too, but they have been closed down under pressure from officials. This recent development shows that services run in the US can’t be safe. US authorities can walk in at any time and request your data or force them to implement backdoors, no matter what security measures the service provider is implementing. And it’s foolish to believe that this is used only against terrorists. It’s enough that a friend of a friend of a friend is targeted for some reason or that there is some business interest that competes with American interests.
  • The safest way to deal with most of the threats is to use end-to-end encryption. For this you need some additional software like Pretty Good Privacy, aka. PGP. It’s a bit of a hassle as both parties need to have compatible encryption programs and exchange encryption keys. But when it’s done you have protection for both stored messages and messages in transit. PGP also provides strong authentication of the message sender in addition to secrecy. This is the way to go if you deal with hot stuff frequently.
  • An easier way to transfer secret stuff is to attach encrypted files. You can for example use WinZip or 7-Zip to create encrypted packages. Select the AES encryption algorithm (if you have a choice) and make sure you use a hard to guess password that is long enough and contains upper and lowercase letters, numbers and special characters. Needless to say, do not send the password to the other party by mail. Agreeing on the password is often the weakest link and you should pay attention to it. Even phone and SMS may be unsafe if an intelligence agency is interested in you.
  • Remember that traffic metadata may reveal a lot even if you have encrypted the content. That is info about who you have communicated with and at what time. The only protection against this is really to use anonymous mail accounts that can’t be linked to you. This article touches on the topic.
  • Remember that there always are at least two parties in communication. And no chain is stronger than its weakest link. It doesn’t matter how well you secure your mail if you send a message to someone with sloppy security.
  • Mails are typically stored in plaintext on your own computer if you use a mail client program. Webmail may also leave mail messages in the browser cache. This means that you need to care about the computer’s security if you deal with sensitive information. Laptops and mobile devices are especially easy to lose or steal, which can lead to data leaks. Data can also leak through malware that has infected your computer.
  • If you work for a company and use mail services provided by them, then the company should have implemented suitable protection. Most large companies run their own internal mail services and route traffic between sites over encrypted connections. You do not have to care yourself in this case, but it may be a good idea to check it. Just ask the IT guy at the coffee table if NSA can read your mails and see how he reacts.

Finally. Sit down and think about what kind of mail secrecy you need. Imagine that all messages you have sent and received were made public. What harm would that cause? Would it be embarrassing to you or your friends? Would it hurt your career or employer? Would it mean legal problems for you or your associates? (No, you do not need to be criminal for this to happen. Signing a NDA may be enough.) Would it damage the security of your country?  Would it risk the life of you or others? And harder to estimate, can any of this stuff cause you harm if it’s stored ten or twenty years and then released in a world that is quite different from today?

At this point you can go back to the list above and decide if you need to do something to improve your mail security.

Safe surfing,

More posts from this topic


Is protection against self-incrimination dead in the digital era? (Poll)

How to balance between privacy and crime fighting? That’s one of the big questions now when we are entering the digitally connected era. Our western democracies have a set of well-established and widely accepted rules that control what authorities can and can’t do. One aspect of this has been in the headlines lately. That’s your right to “plead the Fifth”, as the Americans say. Laws are different in every country, but most have something similar to USA’s Fifth Amendment. The beef is that “No person … shall be compelled in any criminal case to be a witness against himself,…”. Or as often expressed in popular culture: “You have the right to remain silent.” With more fancy words, protection against self-incrimination. What this means in practice is that no one can force you to reveal information if authorities are suspecting you of a crime. You have the right to defend yourself, and refusal to disclose information is a legal defense tactic. But the police can search your home and vehicles for items, if they have the proper warrant, and there’s nothing you can do to stop that. In short, the Fifth Amendment protects what you know but not what you have. Sounds fair. But the problem is that there was no information technology when these fundamental principles were formed back in 1789. The makers of the Fifth Amendment, and similar laws in other countries, could not foresee that “what you know” will expand far beyond our own brains. Our mobile gadgets, social media and cloud services can in the worst case store a very comprehensive picture of how we think, whom we have communicated with, where we have been and what we have done. All this is stored in devices, and thus available to the police even if we exercise our right to remain silent. Where were you last Thursday at 10 PM? Do you know Mr John Doe? What's the nature of your relationship with Ms Jane Doe? Have you purchased any chemicals lately? Do you own a gun? Have you traveled to Boston during the last month? Have you ever communicated with These are all questions that an investigator could ask you. And all may still be answered by data in your devices and clouds even if you exercise your right to remain silent. So has the Fifth Amendment lost its meaning? Would the original makers of the amendment accept this situation, or would they make an amendment to the amendment? The situation is pretty clear for social media and cloud storage. This data is stored in some service provider’s data center. The police can obtain a warrant and then get your data without any help from you.(* Same thing with computers they take from your home. The common interpretation is that this isn’t covered by the Fifth Amendment. But what if you stored encrypted files on the servers? Or you use a device that encrypts its local storage (modern Androids and iPhones belong to this category). The police will in these cases need the password. This is something you know, which makes it protected. This is a problem for the police and countries have varying legislation to address the problem. UK takes an aggressive approach and makes it a crime to refuse revealing passwords. Memorized passwords are however protected in US, which was demonstrated in a recent case. Biometric authentication is yet another twist. Imagine that you use your fingerprint to unlock your mobile device. Yes, it’s convenient. But it may at the same time reduce your Fifth Amendment protection significantly. Your fingerprint is what you are, not what you know. There are cases in the US where judges have ruled that forcing a suspect to unlock a device with a fingerprint isn’t in conflict with the constitution. But we haven’t heard the Supreme Court’s ruling on this issue yet. So the Fifth Amendment, and equal laws in other countries, is usually interpreted so that it only protects information stored in your brain. But this definition is quickly becoming outdated and very limited. This is a significant ethical question. Should we let the Fifth Amendment deteriorate and give crime fighting higher priority? Or should we accept that our personal memory expands beyond what we have in our heads? Our personal gadgets do no doubt contain a lot of such information that the makers of Fifth Amendment wanted to protect. If I have the right to withhold a piece of information stored in my head, why should I not have the right to withhold the same information stored elsewhere? Is there really a fundamental difference that justifies treating these two storage types differently? These are big questions where different interests conflict, and there are no perfect solutions. So I pass the question to you. What do you think? [polldaddy poll=9102679]   Safe surfing, Micke   Image by OhLizz   (* It is this simple if the police, the suspect and the service provider all are in the same country. But it can get very complicated in other cases. Let's not go there now as that would be beside the point of this post.  

September 30, 2015
Hillary Clinton, email scandal, phishing scam

A phishing scam may hurt Hillary Clinton’s career — could it cost you yours?

This email was one of five phishing scams found in the 6,400 pages of Hillary Clinton's emails released on Wednesday. While there's no confirmation that former First Lady fell for the scam, her political opponents are using it to attack her for the security risks of the unconventional private server she used while in office -- even though a recent report found that 1 of 7 emails received on official U.S. Defense Department servers were either spam, phishing or other malware attacks. Receiving such attacks is inevitable. Cyber criminals have long known that one the best ways to hack into something is to simply ask you for the password. This technique has long relied on the fact that most of are used to entering our credentials so if a site looks trustworthy enough, we'll just type our credentials. From there, the bad guys can use these keys to unlock our digital life. As we've become more savvy in recognizing untrustworthy emails like the one above, criminals have taken advantage of our growing desire to share information about ourselves online to pioneer a more advanced technique called "spear phishing," which usually arrives in the form of a personalized email from an person or business you have a relationship with. This sort of attack was pioneered to hack high-value targets like Clinton. The Russian-backed Dukes group used this method in its 7-year campaign against western interests and others. In our Business Insider blog, Eija offers an inside look at how the CEO of a Finnish startup was the victim of an attempted spear phishing. "However, anyone can be a target..." Eija explains. And if you work in the U.S. government your chances of being hit with a very personalized attack have greatly increased as a result of the recent hack of the Office of Personnel Management. “Every bit of my personal information is in an attacker’s hands right now,"Paul Beckman, the Department of Homeland security’s chief information security officer, said at the Billington Cybersecurity Summit in September. "They could probably craft my email that even I would be susceptible to, because they know everything about me virtually.” Beckman said he regularly sends fake phishing emails to his staff to see if they fall for them, and “you’d be surprised at how often I catch these guys.”' Getting caught results in mandatory security training. But even after two or three rounds of instruction, the same people still fall for similar scams. “Someone who fails every single phishing campaign in the world should not be holding a [top secret clearance] with the federal government,” he said. “You have clearly demonstrated that you are not responsible enough to responsibly handle that information.” Beckman said he has proposed that those who prove they cannot detect a scam be stripped of their clearance, which could limit their career possibilities or even cost them a job. If you're the CEO of a startup, you recognize that security of your business is essential to your success. But if you're just an employee, your incentives for protecting intellectual property are nowhere as strong. Criminals only need one victim to make one mistake to succeed. So what are employers to do when education just isn't good enough? How about positive reinforcement for those who successfully avoid a scam? The truth is we're all only as secure as our training and focus. Organizations need to work on the best methods for developing both. Whether it's at work or at home or in the U.S. State Department, you're likely to be faced with a phishing attempt before long. Here's basic guidance from Eija on how to avoid being hooked: Be vigilant when entering your password anywhere Enable two-factor authentication Use Google’s built-in Security Checkup and Privacy Checkup tools Periodically review forwarding and mail filter settings, Connected apps & sites, Devices and Activities, shared files Disable POP and IMAP access if you don’t need them for a desktop or mobile client Cheers, Sandra

September 29, 2015
The Dukes

“The Dukes” – Ask the Experts

Last week, F-Secure Labs published a new study that provides a detailed analysis of a hacking group called “the Dukes”. The Dukes are what’s known as an advanced persistent threat (APT) – a type of hacking campaign in which a group of attackers is able to covertly infiltrate an organization’s IT network and steal data, often over a long period of time while remaining undetected. The report provides a comprehensive analysis of the Dukes’ history, and provides evidence that security researchers and analysts say proves the various attacks discussed in the report are attributable to the Duke group. Furthermore, the new information contained in the report strengthens previous claims that the group is operating with support from the Russian government. Mikko Hypponen has said that attacker attribution is important, but it’s also complex and notoriously difficult, so the findings of the report have considerable security implications. I contacted several people familiar with the report to get some additional insights into the Dukes, the research, and what this information means to policy makers responsible for issues pertaining to national cybersecurity. Artturi Lehtiö (AL) is the F-Secure Researcher who headed the investigation and authored the report. He has published previous research on attacks that are now understood to have been executed by the Dukes. Patrik Maldre (PM) is a Junior Research Fellow at the International Center for Defense and Security, and has previously written about the Dukes, and the significance of this threat for global security. Mika Aaltola (MA) is the Program Director for the Global Security research program at the Finnish Institute for International Affairs. He published an article of his own examining how groups like the Dukes fit into the geopolitical ambitions of nations that employ them.   Q: What is the one thing that people must absolutely know about the Dukes? PM: They are using their capabilities in pursuit of Russian strategic interests, including economic and political domination in Central and Eastern Europe, as well as the Caucasus region, and a return to higher status at the international level. AL: They are a long-standing key part of Russian espionage activity in the cyber domain. MA: The geopolitical intention behind the vast majority of targets. Q: We now know the Dukes are responsible for a number of high profile attacks, and seemingly target information about politics and defense. But what kind of information might they obtain with their attacks, and why would it be valuable? AL: They might obtain information like meeting notes, memos, plans, and internal reports, not to mention email conversations. In essence, the Dukes aim to be a fly on the wall behind the closed doors of cabinets, meeting rooms, and negotiating tables. PM: The targets of the Dukes include government ministries, militaries, political think tanks, and parliaments. The information that can be gained from these organizations includes, among other things, sensitive communication among high-level officials, details of future political postures, data about strategic arms procurement plans, compromising accounts of ongoing intelligence operations, positions regarding current diplomatic negotiations, future positioning of strategic military contingents, plans for future economic investments, and internal debates about policies such as sanctions. MA: The targets are high value assets. Two things are important: data concerning the plans and decisions taken by the targeted organizations. Second, who is who in the organizations, what are the key decision-making networks, what possible weaknesses can be used and exploited, and how the organization can be used to gain access to other organizations. Q: The Dukes are typically classified as an APT. What makes the Dukes different from other APTs? MA: APT is a good term to use with the Dukes. However, there are some specific characteristics. The multi-year campaigning with relatively simple tools sets Dukes apart from e.g. Stuxnet. Also, the Dukes are used in psychological warfare. The perpetrators can even benefit from they actions becoming public as long as some deniability remains. AL: The sophistication of the Dukes does not come as much from the sophistication of their own methods as it comes from their understanding of their targets’ methods, what their targets’ weaknesses are, and how those can be exploited. PM: They are among the most capable, aggressive, and determined actors that have been publicly identified to be serving Russian strategic interests. The Dukes provide a very wide array of different capabilities that can be chosen based on the targets, objectives, and constraints of a particular operation. They appear to be acting in a brazen manner that indicates complete confidence in their immunity from law enforcement or domestic oversight by democratic bodies. Q: There are 9 distinctive Duke toolsets. Why would a single group need 9 different malware toolsets instead of just 1? AL: The Dukes attempt to use their wide arsenal of tools to stay one-step ahead of the defenders by frequently switching the toolset used. MA: They are constantly developing the tools and using them for different targets. Its an evolutionary process meant to trick different “immunity” systems. Much like drug cocktails can trick the HIV virus. PM: The different Duke toolsets provide flexibility and can be used to complement each other. For example, if various members of the Dukes are used to compromise a particular target and the infection is discovered, the incident responders may be led to believe that quarantines and remediation have been successful even though another member of the Dukes is still able to extract valuable information. Q: Many people reading this aren’t involved in geopolitics. What do you think non-policy makers can take away from this whitepaper? AL: This research aims to provide a unique window into the world of the Dukes, allowing people not traditionally involved with governmental espionage or hacking to gauge for themselves how their lives may be affected by activity like the Dukes. PM: It is important for people to understand the threats that are associated with these technological developments. The understanding of cybersecurity should grow to the point where it is on par with the wider public’s understanding of other aspects of international security, such as military strategy or nuclear non-proliferation. This knowledge is relevant for the exercise of fundamental liberties that are enjoyed in democratic societies, including freedom of speech, freedom of the press, freedom of association, as well as of basic rights such as voting in elections. MA: The geopolitical intent is clearly present in this activity. However, the developments in this realm affects other types of cyber-attacks. Same methods spread. There is cross-fertilization, as in the case of Stuxnet that was soon adapted for other purposes by other groups.   F-Secure’s Business Security Insider blog recently posted a quick breakdown on how the Dukes typically execute their attacks, and what people can do to prevent becoming a victim of the Dukes or similar threats. Check it out for some additional information about the Dukes.

September 22, 2015