Email E. Neumann

Email E. NeumannHow stupid is email?

Actually, email is great. It’s robust, widely-supported, and highly accessible (in the 508 and economic senses of the word). The problem is email clients.


A colleague of mine and I once considered starting up a business around a new email client. The problem though, is that it works best when someone send emails using your email client to someone else using your email client. E.g. you can easily implement PGP encryption:

  • if you’ve previously exchanged email, you both have each others’ keys — snap you’re done;
  • if you haven’t, your client asks whether you want it sent insecurely or asks you for authentication information (something you know about the person that a man-in-the-middle probably doesn’t, or an out-of-band mechanism for authentication such as calling you on the phone; and then sends an email initiating a secure authentication process OR allowing them to contact you and opt to receive insecure communication; all this can happen pretty seamlessly if the recipient is using your email client — they get asked the question and if they answer correctly keys get sent).

It’s relatively easy to create a secure encryption system if you (a) opt out of email, and (b) have a trusted middleman (e.g. if both parties trust a specific website and https then you’re done — even a simple forum will work). But then you lose the universality of email, which is kind of important.

The obvious goal was to create a transparently secure email client. The benefits are huge — e.g. spam can be dealt with more easily (even insecure email can be sent with authentication) and then you can add all the low-hanging fruit. But it’s the low-hanging fruit I really care about. After all, I figure if the NSA can hack my storage device’s firmware, my network card’s firmware, and subvert https, encryption standards, and TOR — and that’s just stuff we know about — the only paths to true security are anonymity (think of it as “personal steganography”) or extreme paranoia. When dealing with anyone other than the NSA, Google, China, Iran, etc. you can probably use ordinary caution.

Well, how come Windows Mail / Outlook and Apple Mail don’t do exactly what I’ve just said and automatically handshake, exchange keys and authentication questions, and make email between their own email clients secure? If it’s that easy (and really, it is that easy) why the hell? Oddly enough, Apple has done exactly this (using a semi-trusted middleman — itself) with Messages. Why not Mail?

OK, set all that aside.


  • Why can’t I conveniently send a new message the way I send a reply (i.e. “Reply with new subject and empty body” or “Reply all with new subject and empty body”)? When using an email client most people probably use Reply / Reply All most, then create new message and copy/paste email addresses from some other message second, and create a new message and type in the email address or use some kind of autocomplete last. Furthermore, many replies are actually intended to be new emails to the sender or sender and recipients. Yet no email client I know of supports the second — very frequent usage.
  • Why does my email client start me in the subject line? Here’s an idea: when you create a new email you start in the body. As you type the body the email client infers the subject from what you type (let’s say using the first sentence if it’s short, or the first clause with an ellipsis if that works, or a reasonable chunk of it with an ellipsis otherwise).
  • Why does my OS treat email, IMs, and SMSs as completely separate things? Studies show grown-ups use email and hardly SMS. Younger people use SMS and hardly use email. Both probably need to communicate with each other, and both are generally sending short messages to a person, not a phone number or an email address.
  • (While I’m at it, why does an iPhone treat email and IMs as different buckets? How come they had the nous to merge IMs and SMSs, and even allow semi-transparent switching between secure and free iMessages and less secure and not-necessarily-free SMSs based on whether the recipient was using an Apple device or not? I don’t ask why Android (or heaven forfend Windows) does this because (a) Android generally hasn’t even integrated mailboxes, and (b) don’t expect real UI innovation from Google; they can imitate, but when they originate it tends to be awful — aside from Google’s home page which remains one of the most brilliant UI decisions in history.
  • Oh yeah, and voicemail.


Now imagine a Contacts app that did all this stuff. I’d suggest it needs to be built into email because email is the richest of these things in terms of complexity and functionality, but let’s call it Contact. Consider the nirvana it would lead to:

  • Instantly, four icons on your iPhone merge into one (Mail, Phone, Messages, Contacts (the existence of the last has always bothered me, now it would make sense). Three of those are likely on your home screen; now you have more space.
  • You no longer have to check for messages in four different places (e.g. if you have a voicemail system that emails you transcripts of voicemails, you can mark them both as read in one place, or possibly even have them linked automatically.)
  • Similarly, when you reply to a given message, you can decide how to do so. (Is it urgent? Are they online? Is it the middle of the night? What is your preferred method of communicating with this person?) Maybe even multiple linked channels.
  • Message threads can cross message domains (imagine if you reply to an email with a phone call and Contacts knows this and attaches the record of the call to the thread containing the emails, SMSs, iMessages, voicemails, and so on). Some of this would require cleverness (e.g. Apple owns iMessages, so it could do things like add subject threads to messages on the side, but SMSs are severely constrained and would lose their thread context).
  • Oh, and you can use the same transparent encryption implementation across whichever bands make sense.
  • Obviously some of these things won’t work with some message channels e.g. you can’t do much with SMS because the messages aren’t big enough, but MMS, which is what most of us are using, works fine, similarly Visual Voicemail could support metadata but doing it with legacy voicemail systems isn’t going to happen.

Consider for a moment how much rocket science was involved in getting Continuity to work on iOS and OS X devices. To begin with it requires hardware that isn’t on older Macs and iOS devices. And what it does is pretty magical — I am working on a Keynote presentation, walk over to my Mac and automagically I am working on the same document in the same place. But really, how useful is this really and how often? Usually when I switch devices I am also switching tasks. Maybe that’s because I grew up in a world without Continuity.

Now consider how this stuff would require almost no rocket science and how often it would be useful.