With the NSA data leaks and corporate hacking horror stories fresh in our memory, Americans are looking for new ways to keep the government and other unsolicited third parties out of our day to day communication. Secure email is a particularly relevant tool, especially for business professionals who may have HR or proprietary information that cannot fall into the wrong hands. By now, it is no mystery that the integrity of your information is important.
As far as government security goes, in most cases we have nothing to hide. It’s the principle of the matter. Where do we draw the line between security and free access to everything? When does the focus shift from security to surveillance? For those who are late to the party, that line has grown quite thin.
At the end of the day, we just don’t believe that spying on American citizens and calling it “security” to protect us from ourselves, is a very American thing to do.
In this spirit, I’ve compiled a list of secure email options and written a competitive analysis based on some essential criteria. The criteria are:
- Security
- Experience Design
- Mobile Optimization
- Enterprise Functions
I hope this information proves to be relevant for you, as we work towards a society where universal secure communication is the industry standard.
Mailpile
According to its website, Mailpile is “a project to rescue our personal lives from the proprietary cloud and prevent our conversations from being strip-mined for corporate profit and government surveillance. Mailpile is taking e-mail back.”
With a mission statement that bad-ass, Mailpile is certainly worthy of some of the hype surrounding it.
When it comes to actual security, Mailpile is somewhat lacking. The service operates through POP, IMAP, and SMTP servers, and supports the PGP/MIME and Open PGP standards for encryption and digital e-mail signature. These standards are admittedly flawed in that they do not protect the integrity of the information in the to, from, or subject header lines. Furthermore, there are issues raised in the protection of metadata through Mailpile’s use of Tor. Tor has recently come under criticism due to its inability to protect the anonymity of its users in certain cases.
In most cases, Open PGP requires an encryption key that most users do not use. This could pose issues for Mailpile by sacrificing security for ease of communication between users.
As far as experience design goes, Mailpile is ahead of the curve. The first time logging in, the user is taken on a surprisingly simple and intuitive journey through some high-level functions. The inbox is beautifully organized, with large type, organization, functionality, and advanced settings laid out in a non-intimidating manner. It looks orders of magnitude better than Outlook, and is much less cluttered than Gmail. Relevant action buttons are given priority, and messages appear clean and easy to read. The ability of Mailpile to organize complex information in such a way earns them serious accolades in my book.
Mailpile does not currently plan on releasing a mobile application for Android or iOS.
For businesses considering Mailpile as a solution for their high-level secure communication standards, there are a few important things to note. First, Mailpile’s security mostly comes from its ability to download email from existing mail servers and store it on a computer or personal server. This means that though the information may be secure on the downloaded server, it is still vulnerable on the original servers or through the sending of the communication. Though Mailpile utilizes PGP encryption keys, these are uncommon in every day communication and it is likely that communications sent outside of an organization may still be susceptible to malicious attacks.
That being said, Mailpile is still far more secure than Outlook and Gmail, and manages to organize some high-level functions in a simple way. It also allows for encrypted file storage and other advanced usability settings. All this, combined with a free price-tag, makes Mailpile a good, albeit not perfect, solution for your company’s secure email needs.
Hushmail
Hushmail is a secure email solution that rose in popularity after the infamous demise of Lavabit and Silent Circle. With advanced enterprise functions for businesses subject to the new HIPA regulations, Hushmail is a potentially viable option for healthcare agencies or regular businesses.
Hushmail operates under similar encryption standards to Mailpile and thus suffers some of the same security limitations previously outlined. Furthermore, it utilizes as the outdated and notoriously insecure HTTPS framework for protecting web traffic. In addition to this, Hushmail has recently come under fire for agreeing to compromise its users security with a court order from the Canadian courts. Though this may not seem alarming to somebody who has nothing to hide, users who are serious about security, or those who are looking for an e-mail solution with serious cryptographic integrity may not be best suited by Hushmail. The worry is this: if Hushmail can access its user’s information, what is stopping a malicious third party from doing the same? This approach to information could be seriously flawed based on Kerckhoff’s Principle.
The Hushmail layout is simple, clean, but leaves something to be desired. Though it offers all of the options you would need from an inbox, it is organized in a somewhat cluttered and sporadic way. The compose and check mail functions obviously take priority in terms of screen real estate, but the contacts and settings buttons are given alarmingly low-priority for a web mail application that is built around security. The user profile is, for most cryptographic intents and purposes, nonexistent. There are no serious options for optimizing security or adding additional layers of encryption. Lastly, Hushmail is intended to replace your existing email options so it does not support linking email accounts to be encrypted through Hushmail. For the every day user, this could be a deciding factor.
Hushmail’s saving grace may very well be that it provides mobile optimization, though it does not currently have applications for iOS or Android. Unfortunately, the mobile inbox has weak design elements and offers no functionality beyond writing and receiving emails. This, combined with only the bare minimum in terms of security standards, is enough to suggest that there are significantly better options.
The only reason I can think of that somebody would use Hushmail over its competitors would be its improved premium accounts for businesses in the healthcare sector. It offers HIPAA compliant services by providing a BAA (Business Associate Agreement) with a paid Healthcare services account. The Healthcare plan will run your organization $9.99 per account.
Enigmail
Enigmail is an add-on to the popular Mozilla Thunderbird e-mail client, which allows for e-mails to be signed or encrypted under the same Open PGP standard as Hushmail and Mailpile. Therefore, it is subject to the same security restrictions that were previously mentioned in the section about Mailpile.
Enigmail’s experience design is clunky and outdated, but provides serious capabilities for the advanced user. A serious difficulty for designing UI for products with a highly technical back-end is displaying complex information in a simple and easy-to-understand way. Enigmail does not accomplish this effectively. Encryption information within messages is invasive and confusing to the average user. The interface is dull, and not intuitive. With an intimidating set-up “quick guide” that does not live up to its name, you would likely be a part of the minority if you took the time to register and set up your account. This is definitely a secure e-mail client that was built for the serious cryptographer, who doesn’t mind sacrificing intuitiveness and design for functionality.
Enigmail is not currently optimized for mobile use, and does not offer additional enterprise functionality.
The Future of Secure Email
There has been speculation that Ladar Levison, founder of the late Lavabit, as well as the team at Silent Circle have been cooking up a new standard for end to end e-mail encryption, and information security as a whole. This revolutionary approach to information security will operate on an entirely new protocol called DIME which stands for the Dark Internet Mail Environment. The group has teamed up to create the Dark Mail Technical Alliance, whose mission is “to bring the world our unique end-to-end encrypted protocol and architecture that is the ‘next-generation’ of private and secure email.”
This opens the possibility for an entirely new frontier in secure communication. The DIME protocol would be the first truly “end to end” encrypted solution, and would be released open-source as a strategy to uphold Kerckhoff’s principle. As for when this innovative technology will be available, it is difficult to say.
However, there are a few things that we can say for certain. First, information security is important. Second, the current standards in place for information security have yet to be adopted by critical mass and are, in most cases, lacking in functionality and design. Third, there is a serious opportunity for a company that could provide end-to-end secure information not only between organizations, but within organizations. Whether or not Lavabit will fill this gap, has yet to be seen.
Lastly, this is America damn it! Lets support these projects and put our information back into our own hands.
