Encrypted Email and Security Nihilism

Daniel Kahn Gillmor, reporting on the whole EFAIL thing (short story: even encrypted email isn’t truly safe):

Unfortunately, many of the responses to this report have been close to the line of “security nihilism:” Throwing your hands in the air and saying that because certain important security measures aren’t perfect, we should abandon them altogether. This is harsh and potentially damaging to the best efforts we currently have to protect email and risks leading people astray when it comes to securing their communications.

Personally, I’ve never bothered with encrypted email. As a Gmail user, I’m pretty meh about the fact that Google “reads” it to deliver me contextual ads. I own zero tin foil hats. If you’d like to use me as anecdotal evidence, I’m a decade and a half in and nothing weird/bad has ever happened to my Gmail account.

But I am bullish on general security best practices. You really should have 2FA turned on if you can and have a very secure email password that you change somewhat regularly. If someone gets into your email account, that’s extraordinarily bad. It’s like they have access to every single service you use (that doesn’t use 2FA).  

The Search for the Perfect Email Client

Ars Technica published Inbox zero and the search for the perfect email client, a staff-roundup article all about email preferences. Here’s some choice quotes.

… as anyone who sits through several hours of meetings a day surely knows, staying on top of one’s email becomes a welcome diversion during the many boring bits.

Jonathan Gitlin

Probably not a good sign that a meeting is so un-engaging that you’re literally checking your email during it. But I get it. I stay on top of email everywhere. On the couch, in the line at the grocery, even in bed. How good of an idea that is is debatable, but hey my inbox is usually pretty clean.

I occasionally use both the Outlook and Gmail browser applications to set up filters. The Outlook website is easy to use and looks great, while I’ve always found the Gmail website to be a confusing mess—Gmail.com doesn’t even let you delete messages with your keyboard’s delete key. I prefer non-browser applications, so this isn’t a big deal.

Jon Brodkin

What I find interesting here is that a lot of us have a primary email application we use, but hop around a bit too. We might like a desktop app, but hop over to the web app for some tasks or situations. And use an entirely different app on mobile. Using a service like Gmail or Outlook enables that jumping around. That’s why Google Reader was so nice! It was home base for RSS but we could jump around third-party reader apps easily.

Email, in short, is to be avoided. Unfortunately, email cannot be avoided. My policy is the following: work emails from students and people I know personally get replied to within two working days. Emails from Ars Technica staff are treated much the same, and email from readers is read (but not necessarily responded to) within two days. Emails from family members get replied to within a year. Everyone else can go whistle.

Chris Lee

Chris represents to me the most common email type. Doesn’t like email. Must do email. Fights with himself about email.

I was a huge fan of Sparrow as an email client, and then Google bought it and killed it, which was powerfully disappointing. Inbox by Gmail, the thing that Google sort of made out of Sparrow’s parts, has none of Sparrow’s grace and functionality.


In Sparrow’s absence, I’ve shifted to using Airmail on the desktop for my personal accounts. The interface is an evolution of Sparrow’s (which in turn was an evolution of Tweetie’s). It does everything I want and doesn’t make me angry, and that’s about the best one can say about an email application.

Lee Hutchinson

Almost everyone in this article has mentioned Airmail. No absolutely glowing reviews, but plenty of “this seems to be the best thing out there” sentiments.

I average close to 7000 emails a week now. I’ve taken to using MailSpring, an open-source mail client that I use on Linux (my preferred desktop environment for a number of reasons) to cope with multiple webmail accounts, and I have aggresive spam filtering. I tend to keep emails either in my inbox or in archive so that I can search them for contacts I’ve had on specific topics. I have learned to stop worrying and love my “unread” number.

Sean Gallagher

My god. I wonder if that 7000 is entirely non-Junk and non-Spam. If it is, that seems pretty unreal. Like if Beyonce had a public email address. (Uhm, she doesn’t, and the one she does have changes every week.) I’d really like to talk to a guy like Sean sometime and dig into this is tenable at all.

I try to read every email as it comes in. If I can deal with it immediately—by writing a one- or two-sentence response or by ignoring it entirely—I’ll do so. If it’s something that will take a few minutes and I’m busy with something else, I’ll mark it as unread and come back to it later in the day. If an email requires me to do something that will take more than a few minutes, I’ll make an entry in my to-do list and come back to it later.

Tim Lee

I’d say that sounds mostly healthy, particularly if email is the vast majority of Tim’s job.

Inbox has really good search functions—like, better than Gmail’s traditional interface. It groups related travel emails, for example, automatically pairing flight and hotel information, without any other input from me.

Cyrus Farivar

In my personal email usage, I try to avoid services like Gmail that capitalize on my data these days.

Samuel Axon

There are 159 comments on the post, as I write, so if you’re really into reading about people’s email client preferences, there is plenty to dig into.

My heart

For real though, I’ve definitely had emails I’ve stared at for wayyy too long. Emotionally, I very much want to reply. But my brain can’t come up with the right thing to say.

I wonder if this is a good (and somewhat non-traditional) use of snoozing an email. It’s not that I can’t or don’t want to deal with it right now, it’s that I need to stop looking at it and let my brain sort it out on it’s own time.

Pencil & Paper

Frank Chimero:

Get enthusiasm on the cheap by buying a fancy wooden pencil to write everything down. A $3 pencil is now more exciting than a $2,000 computer. Many people will do the most mundane work just to feel a good tool fly.

Stay on paper as long as possible. Sketch and write things out long-hand, possibly even emails. We all know screens are distracting. It’s much more pragmatic to step away from them for a significant block of time than trying to learn an attentional jiu jitsu that may be impossible. If you think you can’t step away, do it anyway for one day to see how much trouble it causes. That’s useful information.

Have you ever written an email literally on paper first? I’m not sure I ever have. I like the idea though. If anything, I write it in another app (like iA writer) first, because for whatever reason the separation from my actual email app feels appropriate.