Dan rightly notes that a more fulsome implementation is tricky. It also raises fascinating policy questions. Let’s start with the technology. Imagine you violate the classic rule of “Never e-mail while angry,” and fire off a less-than-diplomatic missive to your boss. (You can also substitute “drunk” or “sleep-deprived” for “angry”.) Good sense kicks in a few minutes later. Your options depend on the type of mail system you use:

1. Standard e-mail: you are hosed. Update resume.
2. System that sends e-mail periodically, or when a certain number of messages have accumulated: you can check the Outbox while making an offering to the deity of your choice.
3. System that lets you retract mail: you can submit a retraction request and hope the code works as designed.

An example of #3 is Lotus Domino / Lotus Notes. Lotus calls the feature “message recall,” and it can be set up to retract messages even if the recipient has read them. (Weird, no?) There’s a critical limit, though: “The message recall feature applies only to IBM Lotus Domino servers, and only to mail messages not routed over SMTP servers.” (From the Domino 8.5 Administration Help database) The problem Dan notes applies here: SMTP (Simple Mail Transfer Protocol) has no defined capability to retract messages. It’s up to each mail client to figure out how to do that, if at all. So, once a message leaves the Domino system (for example, it gets transferred to someone using Yahoo! Mail, or Microsoft Outlook), you’re out of luck in terms of getting it back. In other words, it’s proprietary to Domino.

When I worked on Domino at Lotus, e-mail functioned differently: it was like the U.S. postal service. Once an e-mail was sent, it was gone. The developers liked this for policy reasons – it’s a rule, not a standard, for lawyers – and because coding retraction is a nightmare in a world of multiple servers, recipients, read / unread marks, and dual messaging protocols (SMTP and Notes RPC). IBM had a classic Thinkpad commercial where three employers send a snarky e-mail to their boss about needing new computers, only to find that he’s ordered Thinkpads already. “Unsend! Unsend!” they shout, frantically pressing keys on the laptop. We mocked this commercial as an example of Big Blue’s cluelessness, since Domino didn’t do that. But customers really wanted this feature, for obvious reasons. (I used to write e-mail in offline mode, then send messages every 15 minutes, just in case I thought better of something.)

The policy effects are a lot of fun, too. In contract law, we have the mailbox rule for acceptances: acceptance is effective once mailed. What if it’s retracted? Also, what happens if some recipients – say, offerees – have an offer retracted, but others (on non-compliant mail systems) don’t? How would this work for companies that need to archive e-mail to meet SEC or other requirements? If you send a harassing e-mail that’s read, but then disappears, can you avoid a lawsuit? If I copy an e-mail message to an archive or a separate mail folder, what then?

Unsend is fun to think about, but I admit the Lotus implementation of it worries me – particularly since retraction varies with what mail system a recipient is on, and since one can call back messages that have already been read. Gmail’s version seems better, especially as it doesn’t interfere with delivered messages. I’d love to have the option to set a delay in Gmail – say, to hold messages in an outbox for a given period – since 5 seconds is a little short for my brain to function. Until then, I suppose Mail Goggles will have to do…

In addition to a pleasant trip down memory lane (except Jelly Rolls – I hate dueling pianos), this short raises some fun copyright questions. Is this a parody? If so, of what – South Park, Lotusphere, or both? If it’s of Lotusphere, aren’t we in infringing territory (at least in the Ninth Circuit) under Dr. Seuss v. Penguin Books? What about a trademark claim – this mash-up is good enough that I actually wondered if Trey Parker and Matt Stone were involved somehow? (And if so, what does this mean? Only crappy mash-ups are safe from legal liability?) If you’d asked me these questions when I was at Lotus, I’d have looked at you as though you asked about the release plans for Lotus Marmoset 1.0, but now that I’m a lawyer, I sit and ponder them.

Anyway, if you like the vid, here’s another one on Web design that is spot-on.

I remain a huge Lotus Notes fan – primarily for its security and reliability. Of course, I use Notes at a school with an Exchange infrastructure, and root for the Red Sox in a city split between the Yankees and Mets. Up next: I endorse Ralph Nader for the iconoclast trifecta.

This isn’t the first such goof. In fact, a classmate of mine accidentally sent his tale of summer associate leisure to a ream of his colleagues at Skadden Arps rather than just his friend. (It worked out fine for him, but one can only imagine the adrenaline shot on realizing the goof.) It reinforces that information is exceedingly slippery in an age of digital networked communication.

The WSJ writer, Sarah Needleman, proposes some technical ways of providing the pause that refreshes (or causes reflection) – essentially, having one’s e-mail client ask “Are ya sure?” before doing Reply to All or sending to a mailing list. There are two potential problems here. The big one is that people will immediately try to turn off this annoying feature. (Think about Vista’s user account controls.) No one likes it when Notes or Outlook acts like your mom. The second is that such a feature needs to display more information in order to be valuable. If it just asks “Do you want to send to all?”, the answer is, “Of course! That’s why I clicked Send!” The feature ought, therefore, to list all of the recipients when it nags you. There are technical reasons why this might not work – imagine if it’s a mailing list, or if the client is offline and doesn’t have the ability to expand a group into a list – and people are likely just to click past the warning anyway.

Speed is the antithesis of reflection. The brilliance and challenge of e-mail is that it enables near-instantaneous communication. We tend to write things we shouldn’t, and to send them to people we shouldn’t.

So, what if we used technology to force a period of reflection? What if your client let you impose a “cooling-off period” – such that it placed every sent mail in an Outbox, and then sent it after a period of time that you determined via configuration settings? (This works similarly to how mail clients such as Notes and Thunderbird handle things when you send mail when not connected to the Internet.) What if your company made a 60-minute cooling-off period mandatory? Or should we just let instances like this act as cautionary tales, changing perhaps our internal norms but not our mail clients?

The question: do Linux folks care? Do Notes proponents care? Even Linus Torvalds is a skeptic about Linux on the desktop. (Sorry, Tim!)

The fun part is that this is the sequel to Symphony – the original, released in 1984, ran on DOS and was named by John Dvorak as one of the 10 worst software disasters. (Symphony is #4, Microsoft Bob is #10. That hurts.) Thus, IBM is recycling a trademark – and one with questionable associations to boot. (That “boot” may take a while if you use Windows.)

From a classical trademarks perspective, this makes sense. Trademarks allow IBM, as the Lanham Act tells us, to “identify and distinguish [its] goods… from those manufactured or sold by others and to indicate the source of the goods.” Computer users see “Symphony” and know immediately that IBM produces the software. (Let’s assume the users understand that IBM bought Lotus back in the 1990s.) As law students learn, trademarks help reduce consumers’ error costs by helping them find goods generated by a particular producer.

But trademarks do much more than that, and this is what interests me. Do you think Ford has plans to revive the Edsel? No? After all, car consumers probably know instantly that Edsel = Ford. But they also think Edsel = lemon. Trademarks indicate not only source, but also product characteristics. The challenging part is that those characteristics aren’t stable – Symphony, Tab, Taurus – and it’s not clear why we protect a brand trademark that may no longer usefully convey information about what the product is rather than who it’s from.

Technically, trademark law has a tool for this: abandonment. If you take actions that cause your brand to “lose its significance as a mark,” then your mark can be canceled – and your competitors may move to do so. But abandonment is difficult to show, and courts are reluctant to find abandonment. Moreover, it’s not clear what “significance as a mark” means. When Ford slaps Taurus on an entirely different model – the Five Hundred – car buyers still know instantly that the model is a Ford. They just don’t know what the car itself is like. So, if “significance” means only “source designation,” then abandonment doesn’t work well.

I think we need a legal tool to police moves by mark owners that may lead consumers astray when a mark for a model or product type – think iPod or Blackberry – no longer accurately reflects the product’s characteristics. There are at least two hard problems here. First, producers need to innovate; freezing consumer expectations at a given point in time is not helpful. Second, how do we measure and capture the key characteristics of a product that consumers associate with a mark? How much does Coca-Cola have to change the drink before we force them to call it New Coke? I’d love your thoughts on this.

“Best effort” packet routing – as Jonathan Zittrain describes it, the “bucket brigade” where each link in the network tries to pass packets to the next hop, but without guarantees – is less efficient than a protocol that seeks to guarantee transmission and thereby minimizes bandwidth used to communicate. Stateless protocols, such as HTTP, can be less efficient: the server doesn’t keep information about my client or its state and so, by default, each request is a new session. For those of us with a penchant for law and economics as an analytical tool, this state of affairs seems initially sub-optimal.

Yet inefficiency means that data is redundant – cached, preserved, more readily accessible. Years ago, in my life as a sysadmin, I managed to delete my department’s primary database while “cleaning up” our servers. Fortunately, the Lotus Notes replication model means that databases are typically “replicated” (copied and synchronized) widely within a network; I managed to find a nearly-up-to-date replica on a server in Singapore. Inefficiency removed a single point of failure. Many arguments favoring network neutrality emphasize inefficiency’s benefits: rather than tune transmission for high-priority or low-latency applications, “stupid networks” preserve flexibility.

Arguably, there are technical zones where the Internet should be less efficient. One of the characteristics of e-mail that makes spam cheap, and potent, is that a sender can transfer a single copy of a message intended for many recipients in a domain. The receiving mail server will helpfully copy that single copy into each recipient’s mailbox. Require a less efficient model – for example, one message per recipient – and spam’s economics shift dramatically.

My tentative conclusion here is that we should not set efficiency as a goal for legal or technical regulation of Internet-based information; in fact, we should be prepared, even eager, to embrace inefficiency. Hidden virtues are virtues nonetheless. But I’d love to get your thoughts (including, possibly, whether I’ve simply mangled the definition of efficiency!).

This has one interesting note and one virtue. The interesting note is that Notes now creates some competition for Microsoft Office by offering OpenOffice functionality. It’s hardly enough to replace Office as a suite, but 1) it lets cost-conscious companies escape Office licensing fees and 2) most users don’t employ the full range of Office functionality anyway. This will probably have only a minor impact.

The virtue is that it moves Notes towards open standards in terms of document format. States such as Massachusetts are increasingly concerned about being locked into proprietary formats (which both Office and Notes employ natively) for files. Massachusetts has started to move towards ODF, a laudable move. This could have a significant impact, especially if Notes moves towards some sort of open standards object store for the Notes database itself.

Disclosure: I used to work for Lotus, and still use Notes by choice. I own IBM stock, which is currently so far underwater there’s coral growing on it. So, I’m not unbiased here.