With Mailbox For Desktop, We May All Live At The Post Office Again

After years of grieving Eudora, my beloved but long-lost desktop-email client, I’ve found a replacement. It’s called Mailbox.

Starting Tuesday, more people will be able to get their hands on it. Dropbox, which bought Mailbox last year, is opening up its beta program a little wider.

See also: How Mailbox Scaled To One Million Users In Six Weeks

I’ll tell you more about how you can get an invite in a bit. But first, let me tell you a story of love and loss.

Eudora: A Love Story

In 1995, when I was an intern at Mother Jones magazine, my then-boss, Joel Truher, introduced me to Eudora. For the next 16 years, I took Eudora everywhere I went.

Eudora has a charming back story: It was named after Eudora Welty, the author of the short story “Why I Live at the P.O.” Like the protagonist of Welty’s story, we live in our own personal post offices, deluged in digital postcards. While there have been attempts to kill off email, the truth is that it will never stop coming.

At Time Inc., my colleagues and I went through four email systems in the course of eight years. I figured out hacks to make sure that whatever bizarre system my overlords came up with, I could still use clean, simple Eudora.

See also: Innovating The Email Inbox—Without “Delete All”

It had spam filters. It had rules. I could “bounce” emails from one account to another, to deal with the annoyance of people sending work-related emails to personal addresses, or vice versa. And Eudora stored email in a simple, compact, text-based format, making search a dream—as long as I had my laptop with me.


Eudora’s ’90s look (via Copper.net)

I knew that Gmail was making desktop email obsolete. But I had a system that worked, and I was hell-bent on holding onto it as long as I could.

It was actually Apple, not Google, that killed Eudora. I wanted to upgrade to Mac OS X 10.7 to get some new wonder—probably iPhoto’s Photo Stream feature. I didn’t realize that meant saying goodbye to Eudora. Qualcomm, which had bought Eudora some years back, had stopped supporting the software, turning it over to an open-source project which promptly abandoned it. There would never be an update.

I tried to cope. Apple Mail was no substitute. I gave up and started redirecting one of my personal domains to a Gmail account, to gain the benefit of Google’s spam filtering. And unlike Eudora, I had no way of consolidating my multiple email accounts into one interface. 

I hated Gmail disappearing under a mountain of browser tabs, so I created my own Gmail app with Fluid, a tool which turns Web apps into standalone Mac OS X apps. That gave me a little bit of the feel of an old-fashioned desktop email client. But it wasn’t really the same.

More and more, I looked for ways to communicate that bypassed email: Twitter, Facebook, Campfire, Yammer, Skype, Slack, and others.

My most common routine with email these days: Select all. Uncheck one or two emails. Mark as read. Archive. If I were Welty’s postmistress, I’d be dumping postcards into the bins by the fistful.

Why I Love Mailbox (Despite All Its Flaws)

It hasn’t been easy finding an email app I can truly love. I’ve been too wounded by bad relationships and messy breakups with bad software. I didn’t know if I could trust Mailbox. I didn’t know if my heart could open up again.

So we started out slow. Mobile-only, as most modern relationships begin. I learned to swipe right to archive, swipe left to keep. I could reschedule emails to appear at a time when I could deal with them.

See also: Google To World: Encrypted Email Is The New Black

It was beautiful. I fell hard for Mailbox. I even put up with its quirks and limitations. For months, I only used Mailbox to read email, because it didn’t support Gmail aliases, a feature I require in order to send emails from my readwrite.com address. It sounds crazy that I’d switch back and forth between two apps like that, but Mailbox’s central metaphor—the idea of delaying or rescheduling email, like a task to be completed at the appropriate time—was too perfect. It didn’t help Gmail’s cause that its iOS app struggled with performance issues.

Mailbox gradually added my must-have features, including support for aliases and services besides Gmail. I eventually deleted my Gmail app from my iPhone and went Mailbox-only. 

Mailbox-only on mobile, that is. When I got to work, it was back to my desktop—and back to Gmail. Occasionally I’d fish out my phone just to use Mailbox to reschedule an email to appear in my inbox later. If switching between apps just to get a feature seemed crazy, switching between devices must seem downright loony—but that’s what I ended up doing.

Then came Mailbox for desktop. For the past six weeks, I’ve been living in a world where I go from Mailbox on my phone to Mailbox on my Mac. (At present, Mailbox is only available for Mac OS X.)

For email triage, Mailbox is a beautiful thing. But I still find myself switching to my handrolled Gmail app for a few tasks. Gmail’s smooth integration with other Gmail services like Google Calendar and Hangouts is hard to miss. Mailbox for Mac also still has a few flaws which remind me of the early days of Mailbox for iPhone—it keeps forgetting that I prefer my readwrite.com email alias, for example.

I’m willing to forgive Mailbox these shortcomings, though, because I finally have an experience that reminds me of the good old days of Eudora. It takes me back to the time when I lived at the electronic post office.

What Mailbox Is Delivering

On Tuesday morning, Mailbox for Mac is getting distributed to a wider set of beta testers. 

Existing Mailbox users on iOS and Android will get an invitation called a “betacoin,” and they’ll in turn get three betacoins to share with their friends. It’s a strategy of artificial scarcity reminiscent of the old system Google used to limit Gmail signups using invitations—and a spin on the waiting list Mailbox originally created for its mobile app.


Mailbox’s clean interface is a relief for Gmail clutter.

New features include the ability to save drafts, as well as some improvements geared around desktop email, like better keyboard shortcuts.

When I sat down with Sean Beausoleil, Mailbox’s first engineer in its startup days who remains a key member of the Mailbox team at Dropbox, I mentioned some items on my wishlist.

On top: calendar integration. On mobile, I find it fairly simple to switch between Mailbox and Sunrise, a calendar app, to set up a meeting. (Acompli, a Mailbox competitor puts calendaring into its mobile email client, an all-in-one approach I find overly complicated.) On desktop, though, I’d like a one-click switch between email and calendar, like the one I get with Google Apps.

Mailbox doesn’t have any calendar features today, but it’s clearly something Beausoleil and the rest of the team are working out how to deliver.

“When you communicate a lot, calendar is a natural thing” to think about, Beausoleil told me. “You can think of calendar invites as becoming derivative of the conversation, and not explicit. You can figure out when someone needs to meet based on what they’re saying.”


Mailbox for Mac’s message-deferral tool is its key feature.

Another thing Beausoleil and the rest of the Mailbox team are thinking about is tagging. If you’ve ever been unable to find an email thread because your mental categorization of the conversation doesn’t match the literal words that appear in its text, you know why this would be a good thing.

In Eudora, I used to maintain supremely well-organized folders of emails by company, mailing list, and subject. Most people didn’t bother to use emails like I did—and email can only live in one folder at a time.

“Folders are where email goes to die,” says Beausoleil.

Tagging isn’t something Mailbox contemplated when it was a mobile app, Beausoleil said, but they’re thinking about it now for desktop, an environment where adding keywords to make emails more findable makes sense. And it’s a more flexible approach than Gmail’s labels, which assume you’ll only put email in a very limited set of categories.

I still miss Eudora. But I have hope that Mailbox can be a far better postmistress than Eudora ever was.

All I know is that Dropbox better not screw this one up. Because I can’t have my heart broken by an email program one more time.

Photo by Billy Hathorn; Eudora screenshot via Copper.net; Mailbox screenshots courtesy of Dropbox

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