The 80s Software Program That Made Email Famous

A version of this article originally appeared on Tedium, a twice-weekly newsletter that hunts for the end of the long tail.

Email is such a pain in the butt. We’ve been doing everything in our power to fight the influence it has on our lives, to minimize the spam, the marketing, the burden.

That burden leads lots of folks to fruitlessly hunt for the perfect email client in the same way I hunt for the perfect word processor. Others have followed the paths of least resistance: namely, either Gmail or Outlook.

There was a time when we didn’t feel this way, when getting email was actually exciting. The email client Eudora, named for the late American novelist and Pulitzer Prize winner Eudora Welty, was designed to capture this excitement—the idea that mailboxes were no longer tethered to physical space.

But even as die-hard Eudora users held on, it couldn’t. Did we lose something great?

— Steve Dorner, the creator of the Eudora email client, discussing his personal embarrassment over naming the client after the famed author that inspired it, Eudora Welty, whose works include the 1990 short story “Why I Live at the P.O.” Dorner was taken by the idea of a mailbox that comes to you, rather than the other way around, which inspired the name “Eudora.” For her part, Welty, who lived through the successful years of the email client named after her, wasn’t really a computer user herself. “I find it all very mysterious,” she told her local paper, The Clarion-Ledger of Jackson, Mississippi, in 1996, “but I was certainly flattered to be a part of it.” Welty died in 2001. She was 92.

It was a contrast that was too delicious for The New York Times to ignore.

In early 1997, two applications were in the process of taking over the internet, and both had roots in the University of Illinois at Urbana-Champaign, a school that had birthed one of the earliest forms of online culture. One of those applications, Netscape, became a bedrock of how we surf the World Wide Web. The other, Eudora, put a graphical twist on email.

Netscape, of course, helped turn its creator, Marc Andreessen, into a billionaire, and drove a Silicon Valley boom that we’re still seeing reverberations of to this day—in part because Andreessen leveraged his financial success into further financial success and later, a plum role as a venture capitalist.

In contrast, Eudora maker Steve Dorner created an incredibly popular program, beloved by power users at a time when power users dominated the internet. Of the early protocols that ruled the internet, the web and email were the two most important ones—and UIUC was a proving ground for both.

But the Times only showed up at Dorner’s door for a piece about why he had failed to become a multi-millionaire for what he created. The article reads like something of a backhanded compliment. Not that Dorner appeared to mind.

“To have other people use and enjoy your program is probably what a certain breed of programmer is really interested in,” he told the news outlet at the time. “That's the ultimate reward.”

The reason is simple: There were some differences in what Andreessen and Dorner had done. Andreessen was a student at UIUC when he created NCSA Mosaic in 1993, while Dorner was a university employee when he built Eudora in 1988.

Andreessen rebuilt the software under a new name (Netscape) and ownership structure; Dorner did not.

And while Andreessen moved to California, Dorner stayed in Illinois, spending years telecommuting for Qualcomm, which eventually acquired his work from UIUC Dorner’s main job for many years was maintaining Eudora.

(Side note: This is why you should never create something you truly care about under a work-for-hire structure, because you won’t own it.)

Dorner got a long-term gig out of the move, obviously, but it meant that his idea was at the whims of a large company that was better known for designing communications hardware than email clients. Eudora was a loss leader of sorts—while it had a shrink-wrapped version, most people used the free version of the app, the success of which brought Qualcomm name recognition at a time when it was still pretty obscure.

Soon enough, Qualcomm would move to naming football stadiums for that type of name recognition—and Eudora became the app of choice for power users, perhaps at the cost of the broader internet.

• High customization capabilities: Eudora was an incredibly flexible client for its time, allowing users to tweak it in any way they wanted, allowing for both scripting and sophisticated actions. For this reason, Eudora was Apple co-founder Steve Wozniak’s favorite client. Wozniak told Lifehacker in 2009 (!) that he believed it was the most important productivity tool he had: “The reason I do is, it has an incredible feature that every single mail client should have,” he emphasized. “Any feature in the menu list, any action there, can be added as a button.” (Wozniak, remember, made an incredibly nerdy remote control.)
• Fine-toothed filtering: Eudora had the ability to filter out spam, yes, but it was also designed to filter messages with great amounts of detail and sophistication—think Gmail’s search options, but even more in the weeds. In a 1995 episode of the PBS series Computer Chronicles, Times reporter John Markoff explained that Eudora’s filtering capability made it possible for him to parse thousands of messages daily, apparently including one from Apple co-founder Steve Jobs.
• The ability to “redirect” (rather than forward) emails: Forwarding emails is a common functionality of email clients, but it always gets dicey when, say, you want to send a message to someone, but encourage them to respond to the original sender, rather than you. Eudora made it possible to do this with its “redirect” function, something most email clients don’t support today.
• Bottom posting of replies: Perhaps the most controversial feature of Eudora—reflecting an era in which many internet users posted in Usenet newsgroups or listservs—was the concept of “bottom posting,” or putting replies below the original message, rather than above. The internet, driven by clients like Gmail, has largely abandoned bottom posting in email clients, in favor of top posting, but there are still many partisans out there.
• An arcane way for power users to modify the app: Power users are likely familiar with Gmail Labs, Google’s way of allowing under-the-hood modifications to its webmail interface, but it’s nothing compared to x-eudora-setting, a URI-based tool that goes far beyond anything one can do with Gmail. Basically you paste in one of these codes into a blank message, then click on it, and it changes some obscure setting in the app that otherwise is inaccessible through other means. It’s like having a Game Genie for your email client.

“If an e-mail program can survive the merciless scrutiny of the internet community,” a 1995 ad promoting Eudora stated, “it's got to be good.”

Certainly, from a distance, this sounds like a good way to promote a piece of software like this. Lots of people use it, therefore it’s good.

The problem with this line of thought is that the “merciless scrutiny” of the internet circa 1995 means something different than the scrutiny of the internet circa 2017.

For one thing, there’s loads more people. And on top of that, getting online in 1995 required more technical knowledge than it does now, especially if you wanted to use a graphical interface. Back then, before you could even get going on Windows, you had to set up the ability to connect to the internet using Trumpet Winsock, a networking tool for Windows 3.1 that allowed users to connect directly to the net before Microsoft added it to Windows itself.

Winsock, intentionally or not, was a great way of naturally filtering out people whose skills didn’t meet a certain level. Those who couldn’t figure it out could always use America Online.

Starting with Windows 95, operating systems made connecting to the internet a lot easier, of course, and that meant later generations of internet users—the people who failed the Winsock test in prior versions of Windows—needed more help from their email clients.

Customization was great for those who could wrap their heads around something like Winsock, but later internet users simply wanted things to work—and that led them into the arms of webmail clients like Hotmail.

In a 2015 interview with blogger Joe Clark, Dorner made the point that later internet users were less interested in customization than something that worked out of the box. Combined with a rising flood in our inboxes, our collective philosophy around email had simply changed.

“[A] lot of the sort of later development of Eudora was all about harm reduction, really,” Dorner told Clark. “It was about trying to get rid of the incredible volume of spam. … And, you know, people increasingly didn’t want to put in the time to sort things themselves, to manage things, to learn anything. They just wanted it all to be what they wanted without them having any hands-on.”

Modern users are less sophisticated these days, Dorner added, noting that “a lot of what is in the basic DNA of the internet assumes more competence” than many users have.

“You don’t know what’s possible,” wrote Clark, who used Eudora back in the day. “You don’t know what you’re missing.”

We probably don’t. With smartphones being our most common email vector these days, we’ve had to simplify our messaging needs, rely more on machine learning and artificial intelligence to figure out what we don’t want to see, and embrace the reality that while we can customize some things, we’re mostly putting our trust in Microsoft, Google, or some random startup to get things right.

Eudora was a room full of knobs, perfect for tweaking to your heart’s content. But we’re in an era in which it’s preferable—whether or not it’s wise—to hide the knobs away.

— Steve Dorner, discussing his feelings about the eventual demise of Eudora in an interview with blogger Joe Clark. The client was originally discontinued in 2006, but Qualcomm recreated the program as an open-source project based on the code base for the Thunderbird email client. However, within a few years the company had abandoned it. The response to the new effort was mixed—the feedback on the project’s wiki suggested that people who loved Eudora weren’t ready to commit to the new client.

Eudora hasn’t generated a nostalgia movement along the lines of what we’ve seen with video games or old computing platforms like the Amiga, or even a modest revival like we’ve seen with Gopher.

But the Euroda power users who were there in the heady 90s relished the program, and online communities are dedicated to keeping the email client working for those who still love it. Eudora can technically be used in Windows to this day, although it hasn’t worked on MacOS since version 10.6, due to Apple’s architecture change to Intel. Only imperfect replacements exist.

(If there is a modern parallel, it’s probably TweetDeck, the power-user Twitter app that was never quite the same after the social network acquired it, to the point outdated versions remained in heavy use until Twitter shut them down.)

Tech writer Adam C. Engst, who literally wrote the book about how to use Eudora and used the platform as a home base for his long-running newsletter TidBITS, had quite a challenge when he had to move his messages to another client.

“The problem is that my Eudora Folder has somewhere approaching 1 million messages and thousands of attachments, stored in over 600 nested mailboxes,” Engst wrote in 2011. “My Eudora Folder is nearly 8 GB in size, and since it has grown organically over 18 years and innumerable updates to Eudora, having been moved from Mac to Mac repeatedly over that time, corruption is undoubtedly lurking within the files.”

With an inbox that dates to the days of the Macintosh Classic, before even IMAP was in wide use, the cloud wasn’t an option. It took him a lot of testing and a lot of different applications, but he managed to keep most of his emails.

Imagine using something that much, that aggressively, then having to give it up.

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