A Moment to Think

Ever typed up an angry or hasty e-mail message in Outlook, clicked send and then thought better of it?  Most of us have.  And your first instinct was to try and recall that message.  After all, Outlook has a message recall feature, doesn't it?  Well, sort of. 

The reality is that you're probably better off hiring a team of ninjas to break into the recipient's office in the middle of the night and delete the message from their Inbox than using Outlook's recall feature.  Am I exaggerating?  A little.  There is a long list of reasons why message recall in Outlook will fail.  Among them:

  • The recipient has already marked the message as read (such as by opening it).
  • The recipient has moved the message to another folder (or has a rule that does).
  • The recipient isn't using Outlook.
  • The recipient is checking their e-mail using a non-Outlook client including (but not limited to):
    • Outlook Web Access
    • A Blackberry
    • Gmail
    • Their iPhone...
  • The user is forcing all received e-mail into plain text.
  • It's either daytime or nighttime.

O.K., maybe I made that last one up.  In any event, message recall is notoriously unreliable.  In fact, more often than not what it does is leave your original message in place but add a second message that says "Joe Smith would like to recall his message 'Try a breath mint you bozo!'" to their Inbox.  Which more or less guarantees the recipient is going to read your original message, if they haven't already.

So what to do?

Outlook's Rules Wizard to the rescue. These instructions are for Outlook 2007, but you can do substantially the same thing in all relatively modern versions of Outlook.  We're going to create a rule that delays actually sending a message for 3 minutes after you actually click send.  That gives you time to sip your refreshing beverage, take a deep breath and reflect upon what you just sent.  And, if better judgement overtakes you, delete that message before it sends.

First step, start the Rules Wizard.  You'll find it under Tools | Rules and Alerts. Click "New Rule".  At theCreating a rule bottom of the dialog box that results you'll see "Start from a blank rule" and you'll want to choose "Check messages after sending".

Click next.  Uncheck any and all of the conditions then click Next.  Outlook will warn you that this is going to be applied to every message you send, just click "Yes" (we'll add an exception that sends some messages immediately in a moment).

In the actions box you want to click the last box on the list: "defer delivery by a number of minutes." Deferred Delivery Once that's selected look down at the rule description (bottom of the dialog) and click the link that says "a number of". You'll get the Deferred Delivery dialog box where you can set the number of minutes you want to defer by.  I usually set it to "3" but you can pick anything you like.  Then click OK.  Notice that the Rule Description at the bottom now reflects your choice. 

Before you proceed you should also check the box for "Stop Processing More Rules".  That's just good practice unless you have additional rules that have running on messages you send (I'm willing to bet that you don't). 

If you want to change the delay duration later, just click the link (which is now the number) and you'll get the Deferred Delivery dialog box again so you can make changes.  

Click next.  You'll get the Exceptions dialog box.

Now...there may be certain messages that you're sure you do NOT want to defer.  They're hot and they need to go now.  There are a couple of ways you can do this.  The one I recommend is to check theSet an exception for important messages box marked "except if it is marked as importance".  Then in the rule description at the bottom click the link "importance" and in the Importance dialog box set the exception for "High" importance messages.

What that does is that if you have a message that really needs to go now, and you're sure it's ready to go, you can set the message importance to "High" and the rule will let that message go out immediately, without delay.  Be careful with this one...it may be that you're tempted to flag those angry rants as "Important" because in the heat of the moment they feel important but that would defeat the whole purpose of this rule.

You can also use a category.  Create a category that you want to use to flag a message as "Send Now".  You can do that by going to Edit | Categorize | All Categories.  Click "New" and add the new category.

TIP: I wouldn't name that category "Get around the dummy filter" or "S**t I really want to say".  Keep in mind that it's possible your recipient will be able to see that category on the received message.  Name it something cryptic and innocuous like "SN" (for Send Now).

In your rule when you're setting your exceptions instead of (or in addition to) the High Importance exception set an exception for "Except if assigned to SN category".  Rule exceptions are always "Or" exceptions so if EITHER criteria is met the exception is met. When you've got your exceptions defined click Next.

The Delay Delivery RuleLast step.  Here Outlook is asking you to confirm your rule, give it a name, and turn it on.  You can read the text of your rule pretty clearly and it should read essentially as mine does on the left.

Click "Finish" and then click "OK" to close the Rules Wizard dialog box.

Using The Rule

Using this rule is as simple as can be, all you have to do is compose and send e-mail just like you always do.  When you click "Send" your message will appear to send...but it will actually sit in your Outbox for the duration you specified before it goes.  If you decide to stop it, just open the Outbox, select the message you want to cancel, and delete it.

If you want to send the message but edit it first, drag and drop the message from the Outbox to your Drafts folder and then open it from there, edit and resend.  Yes, it will delay for another 3 minutes as if it were new.

If you want a message to go immediately either flag the message as "High Importance" or you can click the dialog launcher on the Options group and set the category to your "SN" category.  Options DialogThe dialog launcher is the little "box-arrow" icon at the very bottom right corner of the options group.

Note that if you have messages in the Outbox when you go to exit Outlook, Outlook is going to prompt you whether you want to send immediately or exit without sending.  Your call - I would generally just send immediately if you're feeling confident in those messages you sent in the last 3 minutes.


E-mail makes it far too easy to say things we don't really mean to say.  While it's still a best practice to not say anything in an e-mail you wouldn't want your grandmother to read on the front page of the New York Times, the Delay Delivery rule can help save you from yourself on those occasions that you say something you didn't mean and don't want to have to depend upon Outlook's unreliable Recall mechanism to take it back.