Innovation in E-mail

E-mail is the oldest form of what we think of as online communications. But even as the physical platforms e-mail is delivered on have gone from room-sized to pocket-sized, its usefulness and ubiquity remain greater than ever. In recent years, many have questioned whether e-mail’s evolution has hit a stopping point, if this technological dinosaur may be going the way of, well, the dinosaurs. This entry’s first part takes a look at the recent history of innovation in e-mail to provide you with an understanding of where we are now. The second part will take a look at what still needs to be done, who’s doing it, and some of my own ideas for new innovations.

E-mail on the Web

The most recent spurt of innovation in e-mail occurred in 2004 when Google announced GMail, a webmail service offering integrated search, logical groupings of e-mails into ‘conversations’, improved organization through use of multiple labels rather than the traditional hierarchy of folders, and an astonishing(for the time) one gigabyte of storage space per user. Google, previously competing with other online juggernauts only through search and contextual advertising, was now competing in an area where Microsoft, Yahoo!, AOL, and others had raked in a steady cash-flow from users for years without offering them almost anything in the way of improvements.

Despite the invite-only status early in GMail’s beta phase(which 3 years later has yet to end), the features and internet buzz around the new service were enough to have invitations that were auctioned on eBay sell for upwards of $601. Whether by prompted by fear of mass exodus from their own services, or simply shamed by their comparatively pitiful offerings(at the time, Hotmail and Yahoo! offered storage space of 2 MB and 4 MB respectively, with no interesting features of note), other web companies quickly responded by increasing storage space and promising to do more2. Other services such as Spymac were already offering more space before GMail, but had neither the public attention or industry presence to push major providers to make improvements.

Since 2004, e-mail has emerged as a small but important battleground among web service providers. In 2004, Yahoo! acquired Oddpost, a webmail service noted for its innovative interface; Bloomba, an e-mail client focused on fast searching of e-mail, was also acquired by Yahoo! when it purchased Bloomba’s parent company Stata labs. Microsoft acquired Lookout Software, maker of a desktop e-mail search tool aimed at Microsoft’s Outlook Express client, in 2004; Sybari Software and Frontbridge Technologies, makers of anti-spam and other e-mail security tools, were acquired separately in 2005. It’s important to note that Oddpost was available since 2000, and Bloomba since 2003. Though both provided features far more advanced than those of major webmail services, they didn’t have the market share or publicity to bring those features to a wider audience, or to compel larger services to do so without the external prodding of a ‘true competitor’ such as Google.

Another internet giant, AOL, acquired Mailblocks in August 2004, entering the webmail market through its sizable instant messenging service, AIM, nine months later under the name AIM Mail. By waiting to enter the market, AOL was able to learn the rules of the game from the sidelines, showing its preparation by launching with 2 gigabytes of storage, spam and virus protection, integration with its instant messenging service, and even an innovative feature that allowed users to ‘unsend’ e-mails sent to another AIM Mail or AOL mailbox. AIM Mail’s interface was more desktop application inspired than the full page changes of traditional webmail services.

2005 saw further improvements in webmail user interfaces of other companies as well. Microsoft began offering Windows Live Hotmail, incorporating the same web development language, Ajax, that makes GMail’s interface more fluid and desktop application-like. Yahoo! Mail Beta made use of the same techniques, having acquired Oddpost’s code base which already incorporated it. In February 2006, GMail integrated its instant messaging program, Google Talk, with it’s e-mail service, allowing users to view any of their address book’s contacts also using GMail as online or offline, in addition to the user’s contacts from their standalone IM program. Yahoo! added the same functionality in February 2007 to a limited but gradually increasing number of users.

*Update 07/02/07*: Since this entry was written, both Yahoo! and AOL have integrated their IM services with their webmail services. Microsoft has yet to do so, mean Yahoo! webmail users are capable of messaging users of Windows Live Messenger(since Yahoo! and Microsoft’s IM networks are joined), before Windows Live Mail users can.

With so many improvements being made to webmail revolving around making the interface more like a desktop application, you might wonder why people are still getting e-mail on their desktops at all these days. The answer of course is that e-mail desktop clients have been polishing, improving, and innovating as much as webmail has.

E-mail on the Desktop

Before GMail, the e-mail of most business and power users was too frequent and took up too much space to be accommodated by free webmail services, requiring either a paid account for increased storage, or the use of a desktop e-mail application such as Microsoft Outlook, which could be configured to receive mail from the account provided by your ISP and/or your webmail service through POP3 or IMAP protocol. As the majority of computers worldwide use a Microsoft operating system, it logically follows that the majority of e-mail is received on the desktop through the company’s bundled application, Microsoft Outlook. In recent years, Outlook has received strong competition from the same corporation challenging Microsoft’s bundled browser. The Mozilla Corporation, a coordinator of open-source software, released Mozilla Thunderbird 1.0 in December, 2004, intending to improve the user experience of desktop e-mail and news interfaces in the same way its browser, Mozilla Firefox, was challenging Internet Explorer.

Although desktop e-mail client statistics can’t be measured as easily as webmail statistics, it is known that Mozilla Thunderbird has been downloaded more than 43 million times3 thus far. Since its release, Microsoft has added calendar integration, an RSS aggregator, improved search, and improved security features to the latest version of its own e-mail client, Outlook 2007. Tellingly, this is the first major improvement to Microsoft’s e-mail client since Outlook 2003. Thunderbird itself has improved, its 2.0 version currently in beta, now featuring ‘tags’ for e-mail messages that will allow users to organize e-mails in the same way as GMail’s ‘labels’, improved search, and plans for tabbed messaging. The last stable version, 1.5 includes a built in phishing detector, integrated podcasting and RSS reader, and message filters that allow automatic replying and forwarding of e-mails.

A notable innovation in desktop e-mail has been created by taking advantage of Thunderbird’s open-source code to create a portable version, Thunderbird Portable, able to be carried on a USB thumbdrive, external hard drive, or any other portable storage device. As most of these devices have simple plug and play capability in addition to ever-increasing amounts of storage space, this has solved the single greatest problem of desktop e-mail clients, lack of access from other computers. So long as you synchronize your thumbdrive with your computer at home, you’ll even have an easy backup in case either device fails. Now users are able to check and carry their e-mail from the library, the office, at school, at internet cafes, at home, at any location with an internet-connected computer, without any of the inconveniences of a webmail service. Of course, USB drives aren’t the only devices carrying your e-mail in your pocket these days.

E-mail on the What!?

Text on cell phones has long since moved out of the domain of your phonebook and the clock. Newer technologies were the first to fulfill the same basic functionality as e-mail: delivering and receiving messages from one person to another. First mobile-to-mobile text messaging allowed short text messages, usually around 250 characters, to be sent to another text-message capable phone. From there it was a short leap to the similar technology of instant messaging, with services like AIM being integrated onto phones so that users on the computer could send IMs received by their contacts on their phones. Only after the introduction of the web browser would the much older technology of e-mail be updated to fit a mobile architecture. Webmail services could be accessed through the browser at the whim of the user. Other than the amazing ability to fit everything onto such tiny screens, not much innovation was involved in accessing webmail. The real innovation came with devices like the BlackBerry, a wireless handheld device that was part miniature computer, part phone, and part personal organizer.

If you recall my earlier mention of POP3 and IMAP protocol, you know they are what make e-mail on the desktop possible. Essentially, they are what make your computer reach-out through the tubes4 of the internet to your ISP or webmail provider and say, “Hey guys, any messages for me?” For personal computers, with AC power or large batteries, it’s no problem to ask this question every five or fifteen minutes(and thankfully servers aren’t as easily annoyed as secretaries). But for a small mobile device with limited bandwidth, querying too frequently would sap battery power while querying infrequently would make users consistently late in receiving their e-mail. BlackBerry’s creator, Research In Motion, created push e-mail protocol(as opposed to pull e-mail POP3) so that when a new e-mail is received by the server(of your ISP or webmail service), it is sent your mobile device without any requests from that device.

With open-source standard versions(and other proprietary protocols by companies like Microsoft) of BlackBerry’s proprietary push e-mail protocol on the rise, more mobile devices now have access to ‘instant’ e-mail. Cell phone providers are now offering better integration with specialized mobile versions of webmail services as well. T-Mobile, Verizon, and other companies offer ’smartphones’ that are made to better provide internet services in addition to standard telephony. More devices offer both constant wireless access and miniaturized or digital display keyboards. Speech-to-text software is also improving, making it possible to dictate your e-mails to a device without a large enough keyboard. Personal computers even smaller than laptops make it possible to access any of the webmail or desktop client technologies described earlier, at anytime through the PC’s wireless connectivity.

Recapping and Recasting

So we have a competitive webmail market, a diversifying desktop client market, and a still emerging mobile e-mail market. Webmail is becoming more desktop-like through its user interface, spam protection, and virus scanning. Desktop clients are becoming more webmail-like through emulating non-hierarchal organization, increasing portability, and online service integration. The full power of the PC is being brought to bear on e-mail through quicker searching and large numbers of user configuration options, while online service providers are making e-mail connect you to more people, more easily, with more than just electronic letters. Mobile devices are making e-mail a continuing communications technology among newer ones. Online presence indicators, GPS locators, news alerts, and an increasing number of services that provide notification through e-mail continue to expand and enhance what e-mail can do for users. Security, spam, viruses, identity verification, and unwanted chain letters continue to challenge and plague users of e-mail services. Next we’ll take a look at what can still be done with e-mail, and who can do it.

Multimedia E-mail

E-mails have long since been home to more than just text, whether it’s the purple-elephant background, star-bullet-point icons of your mother-in-law, or the professional page layouts of eBay and political campaigns. Despite Microsoft’s crippled support of CSS, graphical layouts in e-mail are improving overall. File attachments let you send pictures, documents, mp3 voice or music, and even short video files. But file attachments of audio or video require you to create the file using a recording program and upload it before sending it to a person who must download it and use another program to play the file, sometimes needing to download extra codecs your recording program used before being able to play it themselves. It’s a cumbersome process that doesn’t facilitate communicating through voice or video.

Companies like Springdoo are changing that. Any user with a microphone or a video camera can record directly to the Springdoo site, then send their voice or video message. An e-mail is received that notifies the user the sender has recorded a voice/video message for them, and by pressing the play button contained in the e-mail, they’re sent to a page on the Springdoo site where an embeded media player loads and plays the message, the same kind of player YouTube has used to such wide success.

Springdoo isnt the only company making voice to e-mail easy. Jott allows users to record messages by calling their service from any phone, and speaking their message and the designated recipient. The message is transcribed using speech-to-text technology and sent to the recipient’s e-mail and cell phone, where they can read the transcribed message or listen to the original audio. I’m convinced that speech-to-text is a must-have for any service that wants to combine the best of e-mail and audio. Audio is more personal, more meaningful, and more human, but it’s not convenient. One of the benefits of e-mail is that it’s available at the user’s pleasure, and can be read thoroughly or merely skimmed. Text is also more reproducible. Audio can’t be excerpted(without special software), copied and pasted, or re-arranged. It also can’t be searched.

The next step is to bring embedded players to e-mail itself. Even YouTube videos, when viewed on the site and sent using the”Share” button, only provides a link to the video. Media players should be embedded in the e-mail itself, reducing the number of steps between users and content. Webmail providers should take the initiative and make file attachments more viewable within their own applications. GMail already lets you play attached mp3s without leaving the webmail service, why not videos as well? Why bother with file attachments at all when there are services like Springdoo, you ask? Because the convenience of Springdoo’s direct record, send, play isn’t a substitute for what can be achieved by working on video and audio files on the PC; editing and enhancing to provide more professional content still has its place.

Secure E-mail

The majority of e-mail users, if they know what encryption is, don’t know how it applies to their e-mail or why they should want to use it. As far as they’re concerned, the only people who can read their e-mail are themselves and those they send it to. Unfortunately, that’s simply not true. Who can read your e-mail? Most of your business, school, or organization’s IT support staff. Several technicians at your ISP, the ISP of the person you’re sending to, and any ISP the e-mail is routed through along the way. If you’re using wireless, anyone running a commonly available program called a packet sniffer. Anyone who infects your computer with a virus, or otherwise gains access to your files. Anyone who gains access to the database your e-mail is stored on or the servers of the ISP it goes through. This concern becomes exponentially greater should legislation such as the SAFETY Act(HR 837) pass, Section 6 of which would require ISPs to retain records of the data for an even longer period of time, increasing the risk of message interception by someone gaining unauthorized access. If you would not want the government to monitor all of your phone calls just in case you mentioned abusing a child, why would you want them to monitor all of your e-mail for the same?

Some wonder whether it matters to the average user. The truth is that it’s a mistake to think you need a reason to have your privacy. You are entitled to it, and users should ask why the services they use aren’t providing it. It’s doubly important for business users, government agencies, or anyone who even occasionally writes about something more interesting than their great-aunt Sally(no offense, Sally). Like many problems, lack of encryption is something that can’t easily be solved on an individual level. It needs the support of large companies who can promote and organize it. But there’s still room for 3rd-party tools and add-ons to provide functionality until that happens.

Meaningful Context

Since early versions of Microsoft Outlook, there’s been a method for marking an e-mail you send as ‘Urgent’, causing it to appear in the recipient’s inbox with a red exclamation icon next to it. Though often abused, this tool is an example of early efforts to provide some kind of distinguishment between a fire-at-the-office notice and pictures of your cousin’s new puppies. Most e-mail inboxes are still a common repository for the deluge of e-mails a user receives with no distinguishment between them. It’s possible for a user to create filters that automatically mark or move some of those e-mails, but the services that provide filters rely on the user to specify the settings exactly. After so many years of sorting spam from regular e-mail and other semantic research, surely something has been learned that would enable smarter filters to be applied?

Better yet, why not let users define why they want to filter their e-mail, and give them tools to suit that purpose better. For example, most business users’ primary concern is not being distracted by unimportant e-mails while not missing the important ones. If GMail, which offers filters, could learn to recognize which e-mails each user considered first priority, it could cater to those users by using it’s other tools, like GMail Notifier, alert them for those e-mails only. Third parties using the GMail API could create a tool that notifies users by an automated phone call or SMS message when the user receives such a message.

Learning why users are sorting their e-mail allows tools to be developed that makes e-mail more than just a communication tool, but a personal assistant tool as well. Automatic downloading of image attachments, because your photo album knows who your cousin is, what he’s sending you, and where you want those puppy pictures stored. One-click scheduling on your desktop/online calendar when your dentist/MeetUp/boss e-mails you appointment notifications. There are many possible services that could be developed, and they all rely on putting your e-mails into context.

But context isn’t just about importance and purpose. It’s also about who your contacts are, what your relationship with them is, and your history of contact with them. What if you could see a page that provided daily, weekly, monthly, yearly reports of who your most-frequent contacts are(mutually or one-way contact), your most frequent topics of discussion, your most frequent actions(delete, sorting, reply, forwarding, mark as important) for certain types of e-mails, etc. For some it would be an amusing treat, for others it could provide valuable information on how to better improve your business/life/communications. What if when you received an e-mail from someone new, your e-mail service stepped up and provided the extra info most of us already search for anyways: who is this person? Even just a snapshot of Google search results for their name would be more valuable than only a name and their e-mail address. What if you give your e-mail service permission to connect with your social networks like Facebook and LinkedIn? What if you let it connect to business, school, and organization directories? Providing relevant information in a visually appealing, easily understandable way is challenging, but isn’t ‘Web 2.0′ about making the internet about people, not just about data?

Identity Verification

As challenging as providing more information about the people you’re communicating with is making certain you’re being provided with information about the right people. Phishing scams are all about making you think the sender is someone else. Spam is all about making you think the sender is someone you already know, or want to know. And if you receive an e-mail from Jay Neely, how do you know you’re communicating with the social strategist, and not the preacher or the marina owner? Identity verification is a challenge on all parts of the web, including e-mail. Ironically, e-mail is one of the most frequent solutions on other parts, as sites rely on a user to provide an accurate e-mail address to be able to gain access to their features. Services like DodgeIt and 10 Minute Mail make many e-mail verification systems pointless, as they make creating throwaway e-mail addresses even easier that it traditionally has been with free webmail providers like Hotmail.

Identity on the web is all about trust. Too much trust is placed in appearances, when users assume that because an e-mail address looks professional or has the right name that it’s from the right person. If Jason Kottke were to e-mail me, I would expect it to be from, not If I’m not paying attention though, I could probably be fooled by or jason@kottk√ę.org. Goodmail Systems, partnering with AOL and Yahoo! is offering a solution, CertifiedMail, that’s available to marketing organizations and other businesses, but what’s the solution for your average user?

Elsewhere on the internet, one of the ways of establishing trust is through your network. If people are willing to vouch for you, or even associate with you, then there’s at least a better chance than normal that you’re someone it’s okay for a new user to associate with. Some of the improvements of more meaningful context offered above could assist with that, but what about for people who don’t have or want a network? Should someone automatically be distrusted because they are too independent, or too competitive to have a network? This is where another concept of trust comes in, one that’s older than the internet but has developed in new ways since it’s inception: age.

The older something is, the more trustworthy we assume it to be. Businesses don’t last long if they consistently mistreat customers. And we’re more willing to start a new relationship with something that’s been around for a while since it’s more likely it will continue to be around in the future. Spammers constantly have to register new e-mail addresses because the old ones are quickly black-listed, and phishing scams have a limited amount of time to work in before the real company or person finds out and starts trying to track them down. My proposal is that a new protocol be established to tie the age of an e-mail account with that e-mail address. This information is no doubt already available within the databases of most e-mail services, but it isn’t accessible by the recipients of the e-mail. By making it accessible to all, webmail services specify or let users specify a minimum age of an e-mail address for its e-mails to be received.

This idea has several benefits.:

  • It reduces the use of free webmail services for spam. Unused accounts waiting to reach the minimum age will auto-expire before they reach that minimum. Large groups of accounts registered by spammers that are used to e-mail each other to avoid auto-expiring will result in a pattern identifiable by the webmail service.

  • Having to wait or jump through more hoops to avoid spam detection is by itself a deterrent to engaging in spam.
  • While age-spoofing might be possible, it would have to be done at a point of origin the spammer owns and controls, placing more of the burden of spam costs on them, and also making blocking them or enforcing spam laws easier.
  • This is a human-readable authentication measure, and one that’s easily understandable.
  • The protocol can be extended to allow older e-mails to be linked to newer ones, so that switching services or switching names is still possible without a loss of trust.
  • If this protocol could be reverse-implemented with current e-mail addresses, there would be no waiting period for it’s effectiveness.


These are the four areas I see the most room for innovation in, although inevitably there will be steps forward in ways none of us can predict. The important lessons to take away from the recent history of e-mail is that being an old technology doesn’t make it any less useful in the modern world, only by becoming large or noticeable can a service pressure other services into improving, communications are becoming increasingly platform independent, and far from nearing extinction, e-mail still has a long time to evolve.

Thank you for reading, I hope to hear your own ideas as well as your responses to mine.