Use these Outlook settings to prevent “oh no!” moments after clicking send

How many times have you clicked send on an email only to realize a few seconds later that you’ve accidently emailed the wrong person, sent a snarky comment to an entire list of people, or left an embarrassing typo in the first line?

I don’t mind confessing to a couple of email howlers in my past that illustrate exactly how the settings below can be life savers!

  • A few years ago, when applying for jobs, I sent a resume to the wrong potential employer. Now, incorrectly addressing a job application is poor form. Unsurprisingly, I didn’t hear back.
  • Another time, I typed the “to” address on an important note too quickly and failed to check that the correct address had auto-filled. A day or two later I was left trying to explain to the actual intended recipient why they had never received my important message.

Fortunately, there are a few settings in Microsoft Outlook that can help you avoid these embarrassing moments. Here’s what you need to do.

Disable Auto-Complete for the address line

When you add recipients to a new email in Outlook by typing the address, you’ll notice that Outlook provides suggestions as you type based on your contact list and previously emailed addresses.

Sometimes that’s a useful, time-saving feature. Other times, it creates a high risk that you’ll accidently send an email to the wrong contact. I’ve lost count of the times I’ve received a strange email in my inbox, only to receive a follow up a few minutes later along the lines of: “Sorry! I meant to send that to my colleague Richard in Accounting.”

You might find it easier to simply disable Auto-Complete entirely. Here’s what to do:

STEP ONE

On the File tab choose Options > Mail.

STEP TWO

Under Send messages, uncheck the option Use Auto-Complete List to suggest names when typing in the To, Cc, and Bcc lines.

Turn on MailTips

Every version of Outlook since 2010 has included the MailTips alerts feature, which can help to avoid common email mistakes.

For example, MailTips can be set so that you receive an alert if you’re about to click Reply All to a large recipient list or if you’ve selected a group email address rather than an individual.

Usually, MailTips is automatically enabled. To check that it’s turned on, or to amend the instances in which MailTips will display a warning, follow these steps:

STEP ONE

Open Outlook and select File > Options > Mail. Under MailTips, click MailTips Options. (Note that MailTips will only show if your account uses an Exchange. If you don’t see this option then, sorry, it’s not available to you).

STEP TWO

Check to see that the option Display automatically when MailTips apply is checked and that all of the MailTips to be displayed are selected. Click OK.

Enable deferred sending

Most email clients, Outlook included, are set up to send email as soon as you click Send. That’s where we often get into trouble. Have you ever wished you’d had an opportunity, a few minutes later, to edit a message or stop it from being sent?

That’s where Outlook’s deferred sending rules come into play. By setting up this simple rule, anyone can delay delivery of mail for up to 120 minutes. Here’s how to set it up:

STEP ONE

On the File tab choose Manage Rules & Alert > New Rule.

STEP TWO

In the dialog box that appears, under Start from a Blank Rule, click Apply rule on messages I send, and then click Next.

STEP THREE

Select any conditions you wish this rule to apply to. If you’d like all messages to be deferred, do not select any boxes. Outlook will ask you to confirm that you wish to apply the rule to all messages that you send.

STEP FOUR

Now, in the Select action(s) list, select defer delivery by a number of minutes. You’ll be prompted to edit the rule description. Click on the underlined phrase a number of and enter the number of minutes you’d like your outbound messages to be held before they’re sent. Click OK, then Next, select any exceptions you’d like to the rule (if any), and you’re set!

Tagged under:

4 Comments

  1. Bree Reply

    And what do we do if we find that we do want to edit the offending email? (Actually, my colleague just told me, but I’m suggesting you add this last step, for others, to this excellent article.) Thanks!!

    1. Richard Heinrich Reply

      Thanks, the comment Bree! You’re right, that’s a vital step! The message will remain in your outbox until the amount of time you specified has elapsed. If you click on the outbox and open up the message, you’ll be able to edit the email. —Richard

  2. DJ Reply

    Rich, you are mistaken that “Every version of Outlook since 2010 has included the MailTips alerts feature.” Only 2010, 2013 and 2016 have it. If you look at the Help feature in Outlook it provides this information. Wish I had it!

    1. Richard Heinrich Reply

      Thanks for pointing that out DJ. It’s been in all of the Windows versions of Outlook released since 2010, but you’re right that it isn’t in all because some of the Outlook for Mac versions haven’t had this feature. Thanks the comment!

Leave a Reply to DJ Cancel reply

Share your thoughts

(Your email is for verification only.)

*