Google’s Undo Send feature is better than Outlook Recall Message, but still not totally effective

For whatever reason, the news that Google had upgraded Gmail’s experimental “Undo Send” feature from beta to become a full-blown feature available to all caused quite a fuss last week. The feature has been around since 2009, when it first revealed by Google Labs. It’s a mystery why such a useful option took six years to make the transition.

The way the feature works is quite simple. Edit your Gmail settings to enable Undo Send and set an interval from 5 to 30 seconds as the delay. When you send messages thereafter, an “Undo Send” link is available during the delay. Clicking the link causes Gmail to retrieve the message from its sending queue and place it in the Drafts folder, where it can be edited to remove any of the problematic text that caused you to want to undo the original send.

The intention behind a feature like Undo Send is pretty simple. Rescue a user from the grief caused when they send a message to someone that they didn’t mean to address (for instance, sending a billet doux to an old flame instead of the current love of your life) or if unintended text is included in a message, as in the case when you send a message to your boss to inform them of just how stupid they are in words that the unfortunate recipient can understand.

I like what Google has done and think it useful, but some challenges exist along the way. Some four years ago, I wrote about the futility of attempting to recall a sent message using Outlook’s “Recall This Message” feature (which still exists in Outlook 2016). I pointed out that current email systems are so fast in handling messages that any attempt to retrieve a sent message is impossible because the required message has probably been dispatched well before the user makes their mind up to recall it. In this respect, Google’s implementation is reasonable because you can choose to delay messages by up to 30 seconds before the server processes them. However, the downside is that all messages are delayed by the selected interval, which kind of takes away some of the goodness.

Other problems are shared by the current recall mechanisms. First, we have the scope of influence for these commands, which are limited to the mail system. Gmail is one big mail system and it can control the processing of any message inside the boundaries of Gmail. The same is true of other consumer systems, like Outlook.com. But things are different with commercial email systems. Take an on-premises Exchange server. A message sent from a mailbox might be recallable, but it might also not be, especially if the message is addressed to an external recipient. The same occurs inside Exchange Online where even users in other Office 365 tenants are external recipients and therefore lie outside the boundary for recall.

Note that Gmail only attempts to delay sending a message. It doesn’t attempt to retrieve copies of messages that are sent and have arrived in recipient mailboxes. Once a message has started on its way, Gmail sends it to its destination. I think this is a reasonable and practical approach because there is only one place you can be assured of blocking an outbound message and that’s before it starts its journey through transport processing. Apart from the problem posed by external recipients, Outlook’s offer to attempt to reach out and extract copies of recalled messages in user mailboxes is prone to disappoint even within the same organization as some users might already have read the offending content (and probably shared it with others).

But the single biggest problem that continues to prevent message recall working as well as you’d like continues to be the proliferation of mobile clients. The new Undo Send feature works if you use a browser to work with Gmail. But switch to Apple’s iOS mail client or any of the myriad email clients that run on Android devices (including Outlook for Android) and you’ll be disappointed because no client user interface is available to recall a message. The same is true when mobile clients connect to Exchange.

To be fair to the developers of mobile email clients, there probably isn’t much that they can do about the problem because the protocols that they depend upon to connect their clients to Gmail or Exchange don’t support the notion of message recall or undo send. Most mobile clients connect to Gmail using IMAP4 while ActiveSync (EAS) is the method used for Exchange; neither protocol has ever supported an ability to withdraw a message. As far as the protocols are concerned, clients provide messages to send and the messages are gone as soon as they are transmitted to the server.

A server-side mechanism is probably needed to provide a bullet-proof way to recall messages. This isn’t to negate the value of allowing users to build in a delay before messages are sent. I like that idea, but would prefer if it could be better controlled so that, for instance, the delay might be applied to messages addressed to specific individuals. But the real solution might lie in some artificial intelligence running on the server that examines outbound email to detect lurking issues, perhaps something like the Clutter feature that learns our email habits over time. Only in this case, the software would be looking for faux pas rather than unimportant email.

And then we might have Clippy brought back to inform users when they might need to reconsider with comments like “Excuse me. I noticed that you called your manager a raving idiot. Would you like me to deliver the message?” Wouldn’t that be nice?

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