E-mail security stinks, and that makes hackers (and the NSA) happy

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The Better Mousetrap Making the perfect e-mail client seems like the build-a-better-mousetrap challenge of our day. Every year or so it seems there's another amazing e-mail client released by a startup, that says it has 'reimagined' or 'reinvented' e-mail and how to use it. Some examples include Sparrow (launched in 2011, bought by Google and discontinued in 2012) and Mailbox (launched in 2013 and bought a month later by Dropbox, and announcement of its imminent retirement just this month). This is kind of ironic considering the move away from e-mail to other messaging services, particularly real-time services, such as Slack and Whatsapp. Recently, perhaps due in part to the imminent shut down of Mailbox, another e-mail app called Polymail has been receiving a lot of hype. It is already the fourth most up-voted product on Product Hunt, and it hasn't even launched yet. Seeing the latest e-mail-mousetrap launch reminds me about one of the inherent security problems all of these applications encourage. A Question of Protocol All of these apps rely primarily on the IMAP e-mail protocol (short for Internet Message Access Protocol). That makes a lot of sense as it keeps most of the e-mail management on the server, and allows app developers…

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The history of messaging, and where it’s going

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There are in my view four main phases in the history of online and mobile messaging. The first phase included e-mail and to some extent real-time messaging (in the form of chat rooms), but was strictly within walled gardens. You could only communicate with others using the same proprietary service provider (America Online, Compuserve, Delphi, etc.). The second phase was the beginning of interconnected systems and the Internet. E-mail no longer stayed on a single server, but could go between companies. Real-time messaging, switched from chats that people had to join, to curated lists of friends, the buddy list, which dictated who you could chat with and allowed people to know when you were available for chat. To chat with someone you needed to know their username (or be able to find it in a directory). In some implementations, such as MSN Messenger, the other user had to approve you being able to see if they were online, but in others like AIM, you could see who was online as long as you knew their username (assuming they had not blocked you). The third phase was the emergence of text messaging on cell phones. This includes SMS, which spread initially…

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