Have you ever written an email and clicked the send button only to wish you had given it just another minute or two of thought? Of course, you can always attempt to do a message recall; however, if your recipient has rules turned on to route your messages, they're going to get it anyway. Also, if you're sending to clients who do not honor that request, you're going to be out of luck. So, how can I configure Outlook to save me from myself?

  1. From the Outlook menu bar, choose Tools | Options. You should see the following:

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  2. Click on the Mail Setup tab

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  3. By default, the Send immediately when connected should be checked. You will want to un-check this option box and then click on the Send/Receive… button to take us to the next part

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  4. You should see an All Accounts group already defined. This, by default, will contain everything that you are currently syncing with. This includes things like:
    • Email accounts
    • SharePoint sites
    • RSS Feeds
    • Published calendars
  5. Now, make sure that the Schedule an automatic send/receive every checkbox is checked. Instead of 30 minutes, you may want to adjust down to 2 minutes. This should be enough time for you to reconsider whether or not you really wanted to send that last email or not.
  6. Once you are done setting these options, click on the Close button
  7. Let's send a test message and see what happens.

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    You will notice that the message is queued for delivery in your Outbox. In approximately 2 minutes (or whatever setting you chose), the email will be delivered and cleared from your Outbox. However, if during that time you decide you want to retract that email, it's a lot easier (and safer) to simply delete it from the Outbox than it is to rely upon everything between you and intended recipient to clean it up for you.