Info/Law

As Dan Solove notes at Concurring Opinions, Google’s Gmail service now offers an “unsend” feature: you have a grace period of five seconds after you click “Send” to think better of it. I have to look at the Gmail code to be sure, but I’d guess that Gmail simply waits to do the HTTP POST until the timer expires. Thus, this feature is less about pulling back a poorly-considered message and more about dealing with inadvertent clicks of the Send button.

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…

Filed under: Blogging, ISP, Intermediaries, Internet & Society, Notes