Everyone at some point in their professional or personal life sends an email that they instantly realize – in that moment of extraordinary clarity or lucidity that invariably follows doing something monumentally stupid – they shouldn’t have sent.

What can you do if you somehow cleverly manage to send out a boneheaded, career-limiting message? (Or if you simply realize you’ve sent it to the wrong distribution group, copied someone you didn’t intend to copy, or used wording that you’d like to change…)

The good news: with Outlook (the examples below are for Outlook 2003; the same functionality is available with Outlook 2007, the specific steps will vary slightly) you have two options…

Option 1

First, you can recall the message. Please NOTE: you can recall or replace an email only if its recipient is using Microsoft Outlook and has not read the email or moved it from his or her Inbox.

Here’s how to do it:

a) In the example below I’ve sent a somewhat unflattering message to myself; to recall a message, click on “Sent Items:”

a) Open the email you want to recall or replace and in the email window click on Actions / Recall This Message:

b) Now you can do either of the following: Recall the message or Recall & Replace the message:

To recall the message, click “Delete unread copies of this message;” to recall and replace the message, click “Delete unread copies and replace with a new message.” In either case, click OK; when replacing the original message, you’ll then type a new message. To be notified about the success of the recall or replacement for each recipient, select the “Tell me…” check box. That’s all there is to itit works great as long as your recipients use Outlook and they haven’t read or moved the message from the Inbox.

Option 2

Your second option is a bit different. It has the advantage of allowing you to cancel any idiotic messages to anyone, anywhere, regardless of the email program they’re using; the disadvantage is that you have to come to your senses within a reasonably short amount of time.

This approach involves setting up a very simple rule. From Outlook, click on Tools, then select “Rules and Alerts:”

Doing so will launch the Rules and Alerts dialog box; click on New Rule and then click OK:

This will launch the Rules Wizard. Select “Start from a blank rule” as shown below, and click on “Check messages after sending,” and then click Next:

Don’t check/select any of the options in the next Rules Wizard dialog box – just click Next. Doing so will launch this dialog box; click “Yes:”

In the Rules Wizard which then launches, select the bottom button, “defer delivery by a number of minutes:”

Next click on the underlined “a number of” link; it’ll launch the dialog box shown below. In this example I selected 5 minutes and then clicked “OK” and then clicked on Next…

With the next Rules Wizard, don’t select any of the options:

Simply click Next…

You’ll then be prompted to name the rule. You could name this rule “Oops I did it again,” “Cancel dumbass messages,” or something similarly entertaining; in this example I simply chose “Defer Delivery.” Check the “Turn on this rule” box as well:

And then click Finish. Click OK to the following question:

This will return you to the main Rules and Alerts dialog box – where you started – just click OK.

From this point on, every email you send will basically be put on hold in your Outbox for the number of minutes you’ve selected.

Usually when we have second thoughts about an email or realize that we sent it to the wrong distribution group, we realize the mistake quickly. Setting up this rule will enable you to take advantage of those second thoughts – or moments of clarity – and cancel sending the message. (Simply go to your Outbox and delete or modify the message.)

The only downside to this approach happens when you send a message late in the day and then go to close Outlook within the time limit you’ve selected – you’ll get a message saying you still have messages in your Outbox, asking if you really want to shut down Outlook. Other than that, it couldn’t be simpler.

Hope this helps… just in case you ever need it!

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13 Comments on “Oh crap! I can’t believe I just sent that email!” How to save yourself from sending idiotic messages

  1. Nadine T. says:

    That’s a wonderfully researched and written post, thanks for all the advice!


  2. kc says:

    Thanks Nadine… happy Friday and have a great weekend. Glad the post was of help!


  3. Alisha says:

    This is very helpful for me. I have two accounts in Outlook and it always wants to use the default account rather than the one an e-mail was sent to because I have my e-mail accounts forwarded to one location and using IMAP. So, sometimes I use my personal account to send e-mail for work. I usually realize this after I’ve already hit send and it’s too late to do anything about it.

    I know most of the people at work use Outlook, so the first option would be very handy. Just in case though, I’ll use the second option as well.

    Thanks for sharing!


  4. kc says:

    Thanks Alisha,

    Glad it was helpful to you…

    Have a great weekend.



  5. oftherock says:

    I am subscribed to your blog. Wow… I hope I would not need this. But it is really great to know that there are things you can still do when you sent out an idiotic and career limiting email!

    I hope you have something as well that would apply for web-based emails (yahoo etc)

    Your blog on how to fold the clothes inside the luggage worked for me! I just got back from the trip. It worked.
    Thanks again.


  6. kc says:

    @ oftherock: thanks so much for your kind comments. Sorry I don’t know of anything for web-based emails – except I know there is a service that some law firms use, but can’t find it. It’s just like Option 2 above, but is web-hosted. If I can come up with it, I’ll post another comment.


  7. Eric says:

    One other note on the message recall: it is completely and utterly reliant on the recipients’ willingness to participate in the recall!

    Here are the series of events on a successful recall:

    – You send the message
    – You recall the message
    – Outlook sends the recall message to all recipients
    – The recall message appears as a separate message in the recipient’s mailbox
    – The recipient opens the recall notice
    – Outlook automatically removes the original (recalled) message from your Inbox

    Here’s what USUALLY happens, though:

    – You send the message
    – You recall the message
    – Outlook sends the recall message to all recipients
    – The recall message appears as a separate message in the recipient’s mailbox
    – The recipient sees the recall notice and doesn’t open it
    – The recipient seeks out the original (recalled) message
    – The recipient opens the original message to see what all the fuss was about

    This happens because people are curious by nature. Only time I’ve ever seen a successful recall is when someone is either quickly opening messages and doesn’t notice that the recall notice is actually a recall notice, and/or they are using the “Next Message”/”Previous Message” buttons in open messages to navigate their mailbox.

    The second tip (about the rules to defer sending) is by far the better suggestion. I always advise against recalling messages, as it looks unprofessional and cowardly. If you sent an e-mail by mistake, send a follow-up message apologizing or otherwise explaining how the message got sent in error. Owning the mistake will reflect better on you than trying to erase the evidence and pretending it never happened.

    If it’s something potentially damaging to you or the company, you may wish to inquire with your local IT support on how to have the message removed by your mail admins. Depending on company policy, this may require managerial approval, security approval, or both, but will be the most effective way of reducing or preventing the potential damage.


  8. Eric says:

    Sorry for the multiple posts, but another potential incident that could rear its ugly head with recalls just occurred to me: I call it the “recall flood.”

    In certain configurations (I wish I could recall how this had occurred, but I have seen it happen, and it’s ugly), a recall send TO a Distribution Group that appears to have come FROM that same Distribution Group will result in everyone on that list getting every single notice about the recall succeeding or failing for each recipient. When this happened, hundreds of people were “spammed” with hundreds of success and failure messages. This is much more likely to garner far more enemies than the original message would have, and most people (as noted previously) will likely have also read the original as well, further compounding the issue for you, the click-happy sender.

    Bottom line: recalling a message is ALWAYS a bad idea.


  9. kc says:

    Eric, Completely agree that the Outlook recall feature is clunky, funky and far less than ideal. The best practice is to exercise a little judgment when writing emails – combined with the defer delivery rule. If I’m ever upset or annoyed by something at work, I’ll employ the 12-24 hour sanity check – and only respond then. Thanks for your very thoughtful comments!!!



  10. TK says:

    This is great guys. I think the best workaround to this problem of sending and then recalling is, as kc said, taking your time. But for technical and not so much practical solution, the 2 solutions are also listed, so thanks for that.

    All in all, Outlook does the best job it can to have a mechanism in place to get email to the other user quickly and efficiently while trying to also on the backend offer a way for the quick witted typist to recall the perhaps less than flattering Faux pas he/she just made. It’s a hard balance, and quite frankly, I don’t know how Outlook can do better. It’s a balancing act that truly has no all-sides-win solution, does it?

    Again, thanks for the posts. Great read. ;)


  11. John International says:

    Is recalling or destroying of a sent email without the recipient’s permission not illegal? Once an email has been sent, it become the property of the recipient. Therefore, recalling or destroying the recipient’s mail without his permission is not only unethical but it is also criminal. Has there been any legal precedent like criminal charge for hacking or theft of email because of email recall or email deleting/destruction? Pulling a mail from someone else’s email account without his permission is hacking. Can someone give me some opinions on this? Thanks.


    Kevin Reply:



  12. Sam says:

    what if you only want to recall the message to one person out of a few recipients, who was mistakenly cc’d, as the silly address auto-text put in the wrong perosn with the same first name :¬/??


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