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).  

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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.

AI/Machine Learning and Email

Seems like a natural fit, right? What better data set than decades of email complete with meta data?

I would think that spam filtering may have been one of mankinds first foray’s into machine learning. My Google-based email has been saving me from spam for a decade. We know that spam evolves to fight the machines that keep it down, and yet the machines seem to be winning. Certainly that’s some form of machine learning and not entirely human hand written filters.

We also have some evidence in the form of Gmail’s tabs (the Promo Tab, et al) which attempt to sort your email by type. And Inbox’s bundles which attempt to intelligently group your email types. That reeks of machine learning. Anthony Dm. has done some home-grown work in this area as well.

Today I wondered what would happen if I grabbed a bunch of unlabeled emails, put them all together in one black box and let a machine figure out what to do with them.

Google outright tells us this is the technology they employ. Although this research paper is about more fancy things like improving email search using actual behavior:

we leverage implicit feedback (namely clicks) provided by the users themselves. Using click logs as training data in a learning-to-rank setting is intriguing, since there is a vast and continuous supply of fresh training data.

There is even a company that is focusing on this entirely! Knowmail.

We’ve heard you hate email, so we fixed it!
Personalized artificial intelligence to help you focus on things that matter most, do more with less effort, and balance work and life.

Fascinating stuff.

“Email lists grow slowly, but their growth is sturdier than social networks.”

Robin Rendle, who writes the email newsletter for CSS-Tricks and has a email newsletter of his own called Adventures in Typography, quotes a bit from Robin Sloan’s book How to Make a Book:

Of all the followings you can accrue—on Facebook, Instagram, Twitter, and platforms yet to be invented—one is more important than the rest by an order of magnitude. It’s the group of people who have given you their old-fashioned email addresses and agreed that they would, from time to time, like to hear from you. Even if no one quite loves their inbox, everyone has one. Across generations and geography, through digital fads and fascinations, email is the common denominator, the magic key.

Email lists grow slowly, but their growth is sturdier than social networks. It’s exciting to see the sharp little bursts of attention on the social networks when something you write takes off. But it’s easy come, easy go; as quickly as attention finds you, it moves on, eager for the next thing. Email lists are sturdier and stickier. There is a real sense, you’ll find, of building them one person at a time.

Robin (Rendle) goes on to say about email:

After an email goes out there’s often nothing but radio silence from the other side and then I begin to worry for half a second whether anybody is reading them at all. I probably just have to remember that every social network has been training me as a writer, for the better part of a decade now, to be dependent on those likes and faves and retweets for my emotional well-being.

It’s pretty much radio silence. Once in a while, people respond to the newsletter with something they’d like to share or some little anecdote. I should do a better job at passing those along to the team, but Robin’s point stands, it’s nothing like the engagement feedback you get on other platforms, which is weirdly at odds with the fact that the actual engagement is likely much higher.

Spam vs. Junk

I really think you should be unsubscribing a lot. An inbox full of only things that matter is a good place to be.

But when you’re doing that unsubscribing, what you’re unsubscribing from is junk not spam. Spam, hopefully, is a very small problem for you. Perhaps a few spam emails leak into your inbox a week and you click the button to mark them as spam. Junk is the real problem. Junk is real email that you just don’t care about.

An inbox full of junk is the #1 contributor to email overload that people experience. Their inbox has 2,874 unread emails, because 2,764 of them are junk. That feels like an extraordinary amount of work to come back from. My advice is to chip away at it over time.

What you shouldn’t do is tediously click and delete each one at a time. Just deleting them is a very temporary solution. They’ll be back. Chipping away at it means opening one, hitting that unsubscribe link and following through with that on the web (they’ll try to trick you six ways to Sunday to stay subscribed), and then deleting the email. Don’t worry about them not honoring your unsubscribe or making you a target for more email you don’t want. There are literal laws against that and unsubscribing is effective.

Sometimes it does take a while though.


“Ugjkadgk. I’m terrible at email.”

It’s like a catchphrase these days. Everybody trying to one-up each other about how bad at email they are. You don’t fit in at dinner parties unless you “like all music except country and rap” and “haven’t looked at my inbox in a month.”

It downright scares me when I hear this from otherwise successful people. It’s straight up saying “I’m unreliable” which is a truly bizarre thing to announce, even if it’s true. They’ll gleefully tell you how they just archive massive swathes of emails in an effort to start fresh. A worthy goal, surely, but how many people were just left hanging? Nothing good is going to come from that.

I quite literally don’t want to work with someone, in any capacity, who I can’t expect email responses from. It’s unreliable and unprofessional.

I don’t wanna stress you out, but there is a better way than giving up on your inbox. You can chip away at it. You can be more vigilant at unsubscribing. You can create filters to programmatically remove things. Maybe you can even outsource it to an assistant if you have the means.

Perhaps over time on this blog we’ll gather up as many strategies as we can to fight an unruly inbox.

Emailing Yourself

I email myself. A lot. I’m still trying to figure out if it’s a bad habit or not. It’s a tough call.

By doing it, it’s effectively making my inbox my to-do list. That feels a slightly problematic because it’s a to-do list that isn’t entirely of my own making. It’s letting the world control my to-do list. Not to mention that I already use another app for my to-do list (I like Things).

But somehow it doesn’t bother me that much. It’s just a little reminder to myself to deal with it later. I often end up moving it to my more official to do lists. Or I just deal with the thing right away. Or it was just a link to something interesting anyway so it goes into my separate workflow for that. Emails to myself never seem to feel like a burden.

I’d say 50% of the email I sent to myself is simply a subject line with enough to remember why I’m doing it. For example, I spot a typo in a blog post and can’t fix it right then, so I write an email to myself quick that says “Typo: applience” or whatever the word was.

The other 50% is from Mail To Self, which adds a quick sharing button that blasts whatever I’m looking at on my iPhone to my email.

How often do you email yourself?

Drip Campaigns

Drip emails are those emails you get after creating an account on a website that come after certain periods of time.

Drip, drip, drip, like a leaky faucet, and sometimes just as unwelcome.

But email is such a strong way to talk to users, and companies know it. A well-done drip campaign can educate users and re-engage them. Possibly getting these users to upgrade or lose less of them to churn. I recently signed up for You Need A Budget (YNAB) and actually quite liked their drip emails.

Useful, and hopefully effective drip emails is exactly what we were hoping to do in a recent stab at that at CodePen. But it’s likely we went a little too far, and have reeled it back a little. We’re still trying to figure it out.

Listen to me and my co-workers Jake Albaugh and Marie Mosley talk all about drip email campaigns over on the CodePen Radio podcast.

Unsubscribing

Sometimes I’ll go on an unsubscribing tear. It’ll happen around some fake holiday like Black Friday or Cyber Monday when even the laziest of marketers manage to pull together a DEALS DEALS DEALS email.

I’m sure we’ll all experienced this. Your inbox will fill up with marketing emails from companies you haven’t heard from in ages. Email overload sets in harder than it normally does. So unlike a normal day, where I might just archive a marketing email to be done with it, the overload pushes me into action and I start unsubscribing en masse. I almost can’t wait for another one to show up so I can get myself off that list.

No barricade is too high. I’ll reset my damn password to your app so I can log in and manually adjust my email preferences – a hoop jumping that normally makes my blood boil. 

But lately, I’ve extended this unsubscribing vigor throughout the year. My unsubscribing finger is a hair trigger.

The vigilance feels like it has paid off in that my inbox feels clean and full of only important and relevant things. It’s work, though. I probably unsubscribe from 2-4 things a day. That sounds unreal as I type it, but it’s true. I shop for things online. I buy tickets. I subscribe to services. I test stuff out. I end up on a lot of email lists and it requires constant scrubbing.

It’s like keeping a house clean, isn’t it? To really keep a house clean, you work at it constantly. You do the dishes and sink every day. You sweep up after yourself. You leave rooms a little cleaner than you found them. Then you do bigger cleaning jobs weekly and monthly. You don’t let it become completely filthy and become overwhelmed by the thought of cleaning at all.

You can start today. Unsubscribe from something. Even if you do one a day, you’ll see progress.

Unsubscribing is also a good baby step toward better email productivity in general. If you can’t be bothered to unsubscribe from junk, it’s likely going to be hard to get the rest of that house in order. If you can, you’re already building momentum. 

Slack vs Email

I seem to remember some of Slack’s early marketing was a bit anti-email. Slack is a new way of communicating on a team that stops the need for email. To some degree, I think (and hope) they are right.

I’m betting most of you have heard of Slack, but if not, it’s like a private chat app for businesses and other less formal groups. For example, I have a Slack for CodePen, the business I run. All CodePen employees are in the Slack, and we talk in there every day.

What’s so interesting about Slack is that it’s partially async. It’s real time chat, but I find maybe 50% of communication on Slack is actually real time chat. It’s often a chat that is broken up with significant time delays. Someone leaves a message and someone else answers it an hour later.

I might post a message like this in Slack:

✨Reminder! We have a new thing launching on Monday. 

The draft of the email announcing it is here: 
The Merge Request in GitLab is here: 

Person X, you’re responsible for Y. I’ll be doing Z. Go team 🎉

That’s kind of like an email. I don’t really need a response immediately, it’s just a broadcasting of information. That could have been an email, but I’m glad it’s not. I’m grateful Slack cuts down on that kind of email. Mostly because I know how differently everyone feels about email and how differently everyone handles email. I essentially don’t trust that the email will reach everyone in time, that they will for sure read it, and do what needs to be done. I trust my Slack message more in this circumstance.

Slack is often not that formal. We’re often just chit-chatting about interesting things we’ve seen on the internet, helping each other troubleshoot some code, or even sharing baby pictures in a dedicated channel. Those things aren’t replacing email, for the most part.

This real-time text-based communication is vital for teams. I’ve literally never worked in a tech job, remote or not, without having something like it. The first jobs I had we did it all over AOL instant messages. That evolved and changed into different apps over time, and Slack is just the most recent in that evolution. There has got to be a way to talk your team that is less intense than phone or video, but more synchronous than email. I think we’ll always need that. If we didn’t have Slack now, we’d be using Discord or HipChat or some other app making its way in this space.

Slack is more than just chat, to be fair. They allow for audio, video, and even screensharing as well. What you post in chat can take many forms too, from photos and video to URLs with expanded previews, to snippets of code and long form posts. Add-ons can even completely customize what a message can be. It’s pretty fancy. 

Yet, I wouldn’t call it an email killer. I can’t find any current Slack marketing that claims that it is. In the same way we don’t generally make our address or phone number public, we don’t share a Slack with most of the world.

Personally, even when I do share a Slack with someone I want to get a message to, it’s not 100% that I’ll chose to message them over Slack. Even though there is some level of I’ll get to this as soon as I can async vibe that happens within teams on Slack, sending a private message still feels like it has some urgency to it, which I don’t always want to convey. Almost like you’re avoiding sending an email because you want an answer quicker.

Here’s another little story just to underscore the idea that everyone is different when it comes to communication preferences. My co-founder Tim, it seems to me, does email just fine. But he doesn’t like it. And in fact, he’ll take steps to make sure that any new upcoming situation is mostly handled outside of email.

For example, if we’re about to start working with a new contractor, by the second or third email back and forth with them, they are being invited as a “single channel guest” to our Slack team. Even people like lawyers and contractors who you might not assume are into the idea of installing a new app to talk to one client. I’m almost always surprised how well that works out and that the people are into it.