All digital tools, whether they are hardware or software, should be secure. That is, they should protect you from surveillance, and stop your device from being controlled by others. Sadly, this is currently not the case. For many digital activities, you may end up needing dedicated programs or equipment intended to provide specific security features. Examples we use in this guide include software that allows you to encrypt your messages or files, like PGP.
But given the large number of companies and websites offering secure programs or hardware, how do you choose the one that's right for you?
The first thing to remember before changing the software you use or buying new tools is that no tool is going to give you absolute protection from surveillance in all circumstances. Using encryption software will generally make it harder for others to read your communications or rummage through your computer's files. But attacks on your digital security will always seek out the weakest element of your security practices. When you use a new secure tool, you should think about how using it might affect other ways someone could target you. For example, if you decide to use a secure texting program to talk to a contact because you know that your phone might be compromised, might the fact that you're using this program at all give an adversary a clue that you are talking about private information?
Secondly, remember your threat model. You don't need to buy some expensive encrypted phone system that claims to be “NSA-proof” if your biggest threat is physical surveillance from a private investigator with no access to internet surveillance tools. Alternatively, if you are facing a government that regularly jails dissidents because they use encryption tools, it may make sense to use simpler tricks—like a set of pre-arranged codes—rather than risk leaving evidence that you use encryption software on your laptop.
Given all that, here are some questions you can ask about a tool before downloading, purchasing, or using it.
Even though digital security seems to be mostly about keeping secrets, there's a strong belief among security researchers that openness and transparency leads to more secure tools.
Much of the software used and recommended by the digital security community is free and open source, which is to say that the code that defines how it works is publicly available for others to examine, modify, and share. By being transparent about how their program works, the creators of these tools invite others to look for security flaws, and help improve the program.
Open software provides the opportunity for better security but does not guarantee it. The open source advantage relies in part on a community of technologists actually checking the code, which for small projects (and even for popular, complex ones) may be hard to achieve. When you're considering using a tool, see if its source code is available, and whether the code has an independent security audit to confirm the quality of its security. At the very least, software or hardware should have a detailed technical explanation of how it functions, for other experts to inspect.
No software or hardware is entirely secure. Creators or sellers who are honest about the limitations of their product will give you a much stronger idea of whether their application is appropriate for you.
Don't trust blanket statements that say that the code is “military-grade” or “NSA-proof”; these mean nothing and give a strong warning that the creators are overconfident or unwilling to consider the possible failings in their product.
Because attackers are always trying to discover new ways to break the security of tools, software and hardware often needs to be updated to fix new vulnerabilities. It can be a serious problem if the creators of a tool are unwilling to do this, either because they fear bad publicity, or because they have not built the infrastructure to fix problems.
You can't predict the future, but a good indicator of how toolmakers will behave in the future is their past activity. If the tool's website lists previous issues and links to regular updates and information—like specifically how long it has been since the software was last updated—you can be more confident that they will continue to provide this service in the future.
When security toolmakers build software and hardware, they (just like you) must have a clear threat model. The best creators will explicitly describe what kind of attackers they can protect you from in their documentation.
But there's one attacker that many manufacturers do not want to think about: what if they, themselves, are compromised or decide to attack their own users. For instance, a court or government may compel a company to give up personal data or create a “backdoor” that will remove all the protections their tool offers. You may want to consider the jurisdiction(s) where the creators are based. If your threat is from the government of Iran, for example, a US-based company will be able to resist Iranian court orders, even if it must comply with US orders.
Even if a creator is able to resist government pressure, an attacker may attempt to achieve the same result by breaking into the toolmakers' own systems in order to attack its customers.
The most resilient tools are those that consider this as a possible attack, and are designed to defend against this. Look for language that asserts that a creator cannot access private data, rather than promises that a creator will not. Look for institutions with a reputation for fighting court orders for personal data.
Of course, companies selling products and enthusiasts advertising their latest software can be misled, be misleading, or even outright lie. A product that was originally secure might be discovered to have terrible flaws in the future. Make sure you stay well-informed on the latest news about the tools that you use.
It's a lot of work for one person to keep up with the latest news about a tool. If you have colleagues who use a particular product or service, work with them to stay abreast on what's happening.
We try to ensure that the software and hardware we mention in this guide complies with the criteria we've listed above: we have made a good faith effort to only list products that have a solid grounding in what we currently know about digital security, are generally transparent about their operation (and their failings), have defenses against the possibility that the creators themselves will be compromised, and are currently maintained, with a large and technically-knowledgeable user base. We believe that they have, at the time of writing, the eye of a wide audience who is examining them for flaws, and would raise concerns to the public quickly. Please understand that we do not have the resources to examine or make independent assurances about their security, we are not endorsing these products and cannot guarantee complete security.
One of the most frequent questions asked of security trainers is “Should I buy Android or an iPhone?” or “Should I use a PC or a Mac?” or “What operating system should I use?” There are no simple answers to these questions. The relative safety of software and devices is constantly shifting as new flaws are discovered and old bugs are fixed. Companies may compete with each other to provide you with better security, or they may all be under pressure from governments to weaken that security.
Some general advice is almost always true, however. When you buy a device or an operating system, keep current with its software updates. Updates will often fix security problems in older code that attacks can exploit. Older phones and operating systems are no longer supported, even for security updates. In particular, Microsoft has made it clear that Windows XP and earlier Windows versions will not receive fixes for even severe security problems. If you use XP, you cannot expect it to be secure from attackers. (The same is true for OS X before 10.7.5 or "Lion").