Preventing regrettable e-mail messages

Christopher Breen
16 April, 2009
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We’ve all done it — pressed ‘send’ and wished we hadn’t. But it that email has truly been sent—made its way out of your computer and on to the Internet — there is no way to do this. Your goose is cooked. Rather than wallow in regret, however, you might turn this tragedy into an opportunity by configuring you and your Mac so you can avoid situations like this in the future.

Obviously, the first step is to carefully consider what you’ve written before clicking Send. Unlike with ill-advised conversations—where you can later swear that you said “dollop,” not “trollop” and this was a simple misunderstanding based on excessive cerumen build-up—everything is spelled out in black-and-white in e-mail messages. Should someone need to check the record, it’s easy to do.

Even then, it’s possible to compose a perfectly legitimate message yet mistakenly send it to the wrong person. More often than not, you realise your mistake just seconds after you click Send. The way to deal with this and other regretful messages is to insert a measure of time between when you finish composing a message and sending it.

Apple’s Mail doesn’t include a Send Message Later command, as does Microsoft Entourage. But you can do something similar by changing your habits and putting a couple of handy AppleScripts to good use.

The habit you’ll want to change is clicking Send when you’ve completed a message. Instead, click Save As Draft. This places your message in Mail’s Drafts folder where it sits until you send it. Normally, you’d have to venture into that Drafts folder, open a message, and then click Send to push it along. However, if you’ve downloaded and installed Andreas Amman’s free (though donations are welcome) Mail Scripts, you can send all messages in this folder at one go. This collection of helpful AppleScripts includes Send All Drafts and Schedule Delivery. If you’ve placed composed messages in the Drafts folder, you can send them all by invoking the Send All Drafts script. If you’d like to send the messages in the Drafts folder at a specific time, use the Schedule Delivery script instead.

If you’re a Gmail user and compose and send message online, you’ll want to take a gander at this Gmail blog entry that describes Gmail Labs’ Undo Send option. It can’t do the impossible—retrieve messages that have been sent—but it does put in place a five second delay before a message is sent. If you immediately regret clicking Send, just click the Undo link within five seconds and the message remains your property.

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